(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester → tert-butyl (3S)-1-(1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-yl(methyl)carbamate

HRID 338856Notes

Reaction equation

HRID 338856 reaction equation
FC(F)(F)S(O[CH: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.[CH3:21][N:22]([C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>>[Cl:18][C:15]1[N:14]=[CH:13][C:12]([CH:7]([N:32]2[CH2:33][CH2:34][C@H:30]([N:22]([CH3:21])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:31]2)[C:8]([F:11])([F:10])[F:9])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 867074011-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 86707418tert-butyl (3S)-1-(1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-yl(methyl)carbamateYield 67%

Procedure

Prepared as described in Example 1, Step C, using 1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate (1.50 g, 4.37 mmol) and (S)-tert-butyl methyl(pyrrolidin-3-yl)carbamate (1.2 g, 6.11 mmol) to afford tert-butyl (3S)-1-(1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-yl(methyl)carbamate (1.15 g, 67%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ac5a81b79a244b298504fd802bb0d076
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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