(S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester → (R)-3-(4-Cyano-2-oxo-2H-pyridin-1-yl)-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester

HRID 1752329Notes

Reaction equation

HRID 1752329 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[O:12][C:13]([N:15]3[CH2:19][CH2:18][C@H:17](O)[CH2:16]3)=[O:14])[CH2:3]1)[CH2:9]2.[O:21]=[C:22]1[CH2:27][C:26]([C:28]#[N:29])=[CH:25][CH2:24][NH:23]1>>[OH:1][C:2]12[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH:5]3[O:12][C:13]([N:15]3[CH2:19][CH2:18][C@@H:17]([N:23]4[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:22]4=[O:21])[CH2:16]3)=[O:14])[CH2:11]1)[CH2:9]2

Participants

3

Reactant 2

HCID 58171511(S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl esterHCID 674800042-Oxo-1,6-dihydro-pyridine-4-carbonitrile

Product 1

HCID 58171583(R)-3-(4-Cyano-2-oxo-2H-pyridin-1-yl)-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl esterYield 2%

Procedure

The title compounds were prepared from (S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester (ca. 1:1 mixture of cis- and trans-isomer) and 2-oxo-1,6-dihydro-pyridine-4-carbonitrile following a procedure analogous to that described in Example 77. The isomers were separated by HPLC on reversed phase (acetonitrile/water containing 1.36% trifluoroacetic acid).

Workup

  1. customThe isomers were separated by HPLC on reversed phase (acetonitrile/water containing 1.36% trifluoroacetic acid)

Sources & evidence

ORD record
ord-31bd24c47e3547e090d2b6f06057c1a7
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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