Diisopropylethylamine → {3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}carbamic acid tert-butyl ester

HRID 1182099ノート

反応式

HRID 1182099 の反応式
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][CH:7]2[CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22]Br)([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:13]([O:17][C:18](=[O:24])[NH:19][CH2:20][CH2:21][CH2:22][N:9]1[CH2:8][CH:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:12][CH:11]=2)[CH2:10]1)([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 167807403-(4-Chlorobenzyl)azetidine

生成物 1

HCID 69411053{3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl}carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-(4-chloro-benzyl)-azetidine (1.0 g, 5.50 mmol), (3-bromo-propyl)-carbamic acid tert-butyl ester (1.31 g, 5.50 mmol) and diisopropylethylamine (1.91 ml, 11.0 mmol) in dry dimethylformamide (20 ml) is stirred at ambient temperature for 18 hours. The reaction mixture is partitioned between ethylacetate and water. The organic phase is washed with water and brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 5% methanol in dichloromethane as eluent to afford {3-[3-(4-Chloro-benzyl)-azetidin-1-yl]-propyl]-carbamic acid tert-butyl ester. [M+H] 339.15

後処理

  1. customThe reaction mixture is partitioned between ethylacetate and water
  2. washThe organic phase is washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography

出典と根拠

ORDレコード
ord-ebaec3e3ec054545bb38a819cf009fa8
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

反応ノート

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