(S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate → (3R,4R)-4-azido-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ol

HRID 338988Notes

Reaction equation

HRID 338988 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.[N:21]([C@@H:24]1[CH2:28][NH:27][CH2:26][C@H:25]1[OH:29])=[N+:22]=[N-:23]>>[N:21]([C@@H:24]1[CH2:28][N:27]([C@H:7]([C:12]2[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:26][C@H:25]1[OH:29])=[N+:22]=[N-:23]

Participants

3

Reactant 2

HCID 86707412(S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonateHCID 86707496rac-(3R,4R)-4-azidopyrrolidin-3-ol

Product 1

HCID 86707497(3R,4R)-4-azido-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ol

Procedure

Prepared as described in Example 9B using (S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate (5.06 g, 14.7 mmol) and (3R,4R)-4-azidopyrrolidin-3-ol (2.08 g, 16.2 mmol) in place of (S)-tert-butyl pyrrolidin-3-ylcarbamate in Step D (2.44 g, 52%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cda97e63d5564654b99c4a89356a3295
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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