tert-Butyl (3-(fluoromethyl)pyrrolidin-3-yl)carbamate → tert-butyl 1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)-3-(fluoromethyl)pyrrolidin-3-ylcarbamate

HRID 338979Notes

Reaction equation

HRID 338979 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.[F:21][CH2:22][C:23]1([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:26][NH:25][CH2:24]1>>[Cl:18][C:15]1[N:14]=[CH:13][C:12]([C@@H:7]([N:25]2[CH2:26][CH2:27][C:23]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])([CH2:22][F:21])[CH2:24]2)[C:8]([F:9])([F:10])[F:11])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 19691539tert-Butyl (3-(fluoromethyl)pyrrolidin-3-yl)carbamateHCID 86707412(S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 86707488tert-butyl 1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)-3-(fluoromethyl)pyrrolidin-3-ylcarbamate

Procedure

Prepared as described in Example 9B using (S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate (1.10 g, 3.20 mmol) and tert-butyl 3-(fluoromethyl)pyrrolidin-3-ylcarbamate (0.70 g, 3.21 mmol) in place of (S)-tert-butyl pyrrolidin-3-ylcarbamate in Step D (1.03 g, 78%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3dfba595e73349748234e7abaafc136f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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