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

HRID 237248ノート

反応式

HRID 237248 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-d7215fe8e65d40ad849fbdced4b6d264
出典データセット
uspto-grants-2014_02
特許番号
US08642583B2

反応ノート

読み込み中…