Dimethyl Sulfoxide → 1-Boc-4-formyl-azepane

HRID 1809635ノート

反応式

HRID 1809635 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH:12]([CH:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]1)=[O:11]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68708706Tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate

生成物 1

HCID 588702361-Boc-4-formyl-azepane収率 100.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

At −60° C., a solution of DMSO (1.73 ml, 24.4 mmol) in CH2Cl2 (20 mL) was added dropwise to a 2M solution of oxalyl chloride (1.28 mL, 14.7 mmol) in CH2Cl2 (7 mL). The mixture was stirred for 20 minutes and then a solution of tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate (2.8 g, 12.2 mmol) in CH2Cl2 (7 mL) was added dropwise. The mixture was stirred for 10 minutes and triethylamine (8.51 ml, 61.1 mmol) was slowly added. The reaction mixture was warmed to ambient temperature and water was added. When the mixture became clear, it was extracted with CH2Cl2, the solvent evaporated to afford crude tert-butyl 4-formylazepane-1-carboxylate (2.78 g, 100%).

後処理

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionit was extracted with CH2Cl2
  3. customthe solvent evaporated

出典と根拠

ORDレコード
ord-c3bef9f2948143158dc62773066ae9c7
出典データセット
uspto-grants-2013_01
特許番号
US08362037B2

反応ノート

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