Dimethylformamide → 3-(2-Benzyloxy-5-bromo-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

HRID 237248노트

반응식

HRID 237248 반응식
CN(C=O)C.[C:6]([O:10][C:11]([N:13]1[CH2:16][CH:15]([O:17][C:18]2[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=2[OH:25])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O>[C:6]([O:10][C:11]([N:13]1[CH2:14][CH:15]([O:17][C:18]2[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=2[O:25][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 673444423-(5-Bromo-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 673463273-(2-Benzyloxy-5-bromo-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester수율 99.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a DMF (10 mL) solution of the title compound of Step C (0.52 g, 1.5 mmol), Cs2CO3 (0.54 g, 1.7 mmol) and KI (0.20 g, 1.20 mmol) was added benzyl bromide (0.20 mL, 0.29 g, 1.7 mmol). After 48 h, H2O was added and the mixture extracted with EtOAc (2×). The combined organics were washed with brine (2×) and dried. Silica gel chromatography (5-20% EtOAc in hexanes) gave 0.65 g (99%) of the title compound as a clear oil. 1H NMR (CDCl3): 7.42-7.36 (m, 3H), 7.34-7.31 (m, 2H), 7.03 (dd, J=8.6, 2.3 Hz, 1H), 6.81 (d, J=8.6 Hz, 1H), 6.70 (d, J=2.3 Hz, 1H), 5.09 (s, 2H), 4.88-4.83 (m, 1H), 4.26 (ddd, J=9.7, 6.5, 0.9 Hz, 2H), 4.05 (dd, J=9.8, 4.0 Hz, 2H), 1.45 (s, 9H).

후처리

  1. extractionthe mixture extracted with EtOAc (2×)
  2. washThe combined organics were washed with brine (2×)
  3. customdried

출처 및 근거

ORD 기록
ord-d7215fe8e65d40ad849fbdced4b6d264
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642583B2

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