(S)-tert-butyl 2-tert-butoxyethyl(pyrrolidin-3-yl)carbamate → tert-butyl 2-tert-butoxyethyl((S)-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-yl)carbamate

HRID 338899Notes

Reaction equation

HRID 338899 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.[C:21]([O:25][CH2:26][CH2:27][N:28]([C@H:36]1[CH2:40][CH2:39][NH:38][CH2:37]1)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][CH2:26][CH2:27][N:28]([C@H:36]1[CH2:40][CH2:39][N:38]([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])[CH2:37]1)[C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:22])([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 70984012(S)-tert-butyl 2-tert-butoxyethyl(pyrrolidin-3-yl)carbamateHCID 86707412(S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 86707441tert-butyl 2-tert-butoxyethyl((S)-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-yl)carbamate

Procedure

Prepared as described in Example 9B, Step D, using (S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl trifluoromethanesulfonate (1.50 g, 4.37 mmol) and (S)-tert-butyl 2-tert-butoxyethyl(pyrrolidin-3-yl)carbamate (2.0 g, 6.98 mmol) in place of (S)-tert-butyl pyrrolidin-3-ylcarbamate (1.69 g, 81%)

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fd849f08e0cc4201a9db3cd0a0120d36
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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