Benzyl (3r,4s)-4-hydroxypyrrolidin-3-ylcarbamate → benzyl (3R,4S)-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)-4-hydroxypyrrolidin-3-ylcarbamate

HRID 338943Notes

Reaction equation

HRID 338943 reaction equation
FC(F)(F)S(O[C@@H:7]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:8]([F:11])([F:10])[F:9])(=O)=O.[OH:21][C@H:22]1[CH2:26][NH:25][CH2:24][C@H:23]1[NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[Cl:18][C:15]1[N:14]=[CH:13][C:12]([C@@H:7]([N:25]2[CH2:26][C@H:22]([OH:21])[C@H:23]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:24]2)[C:8]([F:11])([F:10])[F:9])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 76849151Benzyl (3r,4s)-4-hydroxypyrrolidin-3-ylcarbamateHCID 86707412(S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 86707466benzyl (3R,4S)-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)-4-hydroxypyrrolidin-3-ylcarbamate

Procedure

Prepared as described in Example 9B using (S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate (1.06 g, 3.08 mmol) and benzyl (3R,4S)-4-hydroxypyrrolidin-3-ylcarbamate (0.802 g, 3.39 mmol) in place of (S)-tert-butyl pyrrolidin-3-ylcarbamate in Step D (1.16 g, 88%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7be1949908d7473fa2cb0620aee0403e
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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