A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation

Gregory Carr; Sam Butterworth; Phil Walker; Folkert Reck; Bolin Geng; Lakshmipathi Pandarinathan

doi:10.1055/s-0031-1289724

A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation

Gregory Carr^*
, Sam Butterworth
, Phil Walker
, Folkert Reck
, Bolin Geng
, Lakshmipathi Pandarinathan

^*Corresponding author for this work

Pharmacy

AstraZeneca
AstraZeneca plc

Research output: Contribution to journal › Article › peer-review

Abstract

A robust and scalable synthesis of (R)-methyl 2-[(1r,4R)-4-(tert- butoxycarbonylamino)cyclohexyl]-2-(2-nitrophenylsulfon-amido)acetate is reported. This serves as a scaffold for the preparation of trans-substituted aminocyclohexanes. The key synthetic step is the reduction of d-4-hydroxyphenylglycine, or a protected equivalent, to achieve the required regiochemistry across the cyclohexyl ring.

Original language	English
Pages (from-to)	875-880
Number of pages	6
Journal	Synthesis: journal of synthetic organic chemistry
Volume	44
Issue number	6
DOIs	https://doi.org/10.1055/s-0031-1289724
Publication status	Published - 2012

Keywords

chirality
diastereoselectivity
hydrogenation
protecting groups
reduction

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10.1055/s-0031-1289724

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Carr, G., Butterworth, S., Walker, P., Reck, F., Geng, B., & Pandarinathan, L. (2012). A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation. Synthesis: journal of synthetic organic chemistry , 44(6), 875-880. https://doi.org/10.1055/s-0031-1289724

@article{dd516ec85077477da781d56c502ad2b6,

title = "A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation",

abstract = "A robust and scalable synthesis of (R)-methyl 2-[(1r,4R)-4-(tert- butoxycarbonylamino)cyclohexyl]-2-(2-nitrophenylsulfon-amido)acetate is reported. This serves as a scaffold for the preparation of trans-substituted aminocyclohexanes. The key synthetic step is the reduction of d-4-hydroxyphenylglycine, or a protected equivalent, to achieve the required regiochemistry across the cyclohexyl ring.",

keywords = "chirality, diastereoselectivity, hydrogenation, protecting groups, reduction",

author = "Gregory Carr and Sam Butterworth and Phil Walker and Folkert Reck and Bolin Geng and Lakshmipathi Pandarinathan",

year = "2012",

doi = "10.1055/s-0031-1289724",

language = "English",

volume = "44",

pages = "875--880",

journal = "Synthesis: journal of synthetic organic chemistry ",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "6",

}

Carr, G, Butterworth, S, Walker, P, Reck, F, Geng, B & Pandarinathan, L 2012, 'A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation', Synthesis: journal of synthetic organic chemistry , vol. 44, no. 6, pp. 875-880. https://doi.org/10.1055/s-0031-1289724

A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation. / Carr, Gregory; Butterworth, Sam; Walker, Phil et al.
In: Synthesis: journal of synthetic organic chemistry , Vol. 44, No. 6, 2012, p. 875-880.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation

AU - Carr, Gregory

AU - Butterworth, Sam

AU - Walker, Phil

AU - Reck, Folkert

AU - Geng, Bolin

AU - Pandarinathan, Lakshmipathi

PY - 2012

Y1 - 2012

N2 - A robust and scalable synthesis of (R)-methyl 2-[(1r,4R)-4-(tert- butoxycarbonylamino)cyclohexyl]-2-(2-nitrophenylsulfon-amido)acetate is reported. This serves as a scaffold for the preparation of trans-substituted aminocyclohexanes. The key synthetic step is the reduction of d-4-hydroxyphenylglycine, or a protected equivalent, to achieve the required regiochemistry across the cyclohexyl ring.

AB - A robust and scalable synthesis of (R)-methyl 2-[(1r,4R)-4-(tert- butoxycarbonylamino)cyclohexyl]-2-(2-nitrophenylsulfon-amido)acetate is reported. This serves as a scaffold for the preparation of trans-substituted aminocyclohexanes. The key synthetic step is the reduction of d-4-hydroxyphenylglycine, or a protected equivalent, to achieve the required regiochemistry across the cyclohexyl ring.

KW - chirality

KW - diastereoselectivity

KW - hydrogenation

KW - protecting groups

KW - reduction

UR - https://www.scopus.com/pages/publications/84858081956

U2 - 10.1055/s-0031-1289724

DO - 10.1055/s-0031-1289724

M3 - Article

AN - SCOPUS:84858081956

SN - 0039-7881

VL - 44

SP - 875

EP - 880

JO - Synthesis: journal of synthetic organic chemistry

JF - Synthesis: journal of synthetic organic chemistry

IS - 6

ER -

A multikilogram-scale synthesis of (R)-methyl 2-[(1r,4R)-4-(tert-butoxy- carbonylamino)cyclohexyl]-2-(2-nitrophenylsulfonamido)acetate - A doubly protected building block with three points of variation

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