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

HRID 1887

반응식

HRID 1887 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

5

반응물 4

HCID 1146TrimethylamineHCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 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.

후처리

  1. temperaturewas heated
  2. temperatureat reflux under N2 for 24 hours
  3. concentrationThe mixture was concentrated to dryness
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThe solution was washed with satd
  6. concentrationNaHCO3 and water, then concentrated
  7. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-3c14aa7c3cf94af8afc09046f03b475b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726182

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