Benzylamine → (R)-3-Benzylamino-1,1,1-trifluoro-propan-2-ol

HRID 922771노트

반응식

HRID 922771 반응식
FC(F)(F)S([O-])(=O)=O.[Li+].[F:10][C:11]([F:16])([F:15])[C@@H:12]1[O:14][CH2:13]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([NH:24][CH2:13][C@@H:12]([OH:14])[C:11]([F:16])([F:15])[F:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 7016923(2R)-2-(trifluoromethyl)oxirane

생성물 1

HCID 1477381(R)-3-Benzylamino-1,1,1-trifluoro-propan-2-ol수율 79%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of lithium trifluoromethanesulfonate (1.43 g, 9.17 mmol) in CH3CN (30 ml) was added (R)-(+)-3,3,3-trifluoro-1,2-epoxypropane (10.77 g, 96 mmol) slowly at −10° C. After 5 minutes benzylamine (10 ml, 92 mmol) was added slowly. The mixture was allowed to warm as the bath warmed to rt overnight. The mixture was concentrated. The crude product was subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient) to afford (R)-3-(benzylamino)-1,1,1-trifluoropropan-2-ol (4-2, 15.9 g, 79%) as a white solid. LRMS m/z (M+H)+ 220.2 calc. 220.1 found.

후처리

  1. temperatureto warm as the bath
  2. concentrationThe mixture was concentrated
  3. customwas subjected to silica gel chromatography (330 g, 0-50% EtOAc/hexanes, 10 minute gradient)

출처 및 근거

ORD 기록
ord-5e4e0ea6ec8b47a4ad1e0259f7c41e92
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278960B2

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