Trimethylamine → 1-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidine

반응식

[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:16]([F:19])([F:18])[F:17])(C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.C[N:38]([CH3:40])C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:38][C:40]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:27])([C:16]([F:17])([F:18])[F:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

반응물 4

HCID 1146Trimethylamine

HCID 6386tert-Butanol

HCID 199401P,P-Diphenylphosphinic azide

HCID 196913671-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acid

생성물 1

HCID 196914881-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidine수율 96.7%

실험 절차

A mixture of 1.42 g of the compound from step 454a, 1.71 g of diphenylphosphoryl azide, 12.3 g of t-butanol and 0.627 g of trimethyl amine was heated at reflux under N2 for 24 hours. The mixture was concentrated to dryness, and the residue was dissolved in methylene chloride. The solution was washed with satd. NaHCO3 and water, then concentrated. The residue was chromatographed on silica gel to give 1.73 g of the title compound.