3-Fluoro-4-methylaniline → (RS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(3-fluoro-4-methyl-phenylamino)-butan-2-ol

HRID 527957

반응식

HRID 527957 반응식
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[CH3:22])[NH2:18]>CC#N>[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:11][NH:18][C:17]1[CH:19]=[CH:20][C:21]([CH3:22])=[C:15]([F:14])[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 99573-Fluoro-4-methylanilineHCID 11030897(R)-tert-butyldimethyl(2-(oxiran-2-yl)ethoxy)silane

생성물 1

HCID 66954684(RS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(3-fluoro-4-methyl-phenylamino)-butan-2-ol수율 93.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

To a solution of (RS)-tert-butyl-dimethyl-(2-oxiranyl-ethoxy)-silane (4.4 g, 200 mmol; prepared as in J. Org. Chem. (2008), 73, 1093) in MeCN (60 mL) was added LiClO4 (6.31 g, 3 eq.). 3-fluoro-4-methylaniline (commercial; 2.28 g, 0.92 eq.) was added and the mixture was stirred at 50° C. for 5 h. The solvent was removed under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:25:2) to afford the title intermediate as a brown oil (5.56 g, 86% yield).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by CC (DCM/MeOH/NH4OH 1000:25:2)

출처 및 근거

ORD 기록
ord-67b156c311ce49a3ba76b8e47ddece6f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346804B2

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