Chloroform → HCID 131730260、化合物

HRID 390086ノート

反応式

HRID 390086 の反応式
C([N:8]1[CH2:12][CH:11]2[CH2:13][O:14][C:15]([CH3:19])([CH3:18])[O:16][CH2:17][CH:10]2[O:9]1)C1C=CC=CC=1.C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].C(Cl)(Cl)Cl>C(O)C.CO.[Pd]>[OH:9][CH:10]1[CH2:17][O:16][C:15]([CH3:18])([CH3:19])[O:14][CH2:13][CH:11]1[CH2:12][NH:8][C:28](=[O:29])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

8

反応物 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 66954045(3Ar/s,8ar/s)-2-benzyl-6,6-dimethylhexahydro-[1,3]dioxepino[5,6-d]isoxazole

生成物 1

HCID 131730260HCID 131730260、化合物収率 63.3%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

To a solution of (3aR/S,8aR/S)-2-benzyl-6,6-dimethylhexahydro-[1,3]dioxepino[5,6-d]isoxazole (10.4 g, 39.5 mmol) in ethanol (150 mL) was added 10% Pd/C (2.5 g) and the mixture was stirred under a hydrogen atmosphere. After 2 days the solids and solvent were removed. A solution of the residue in methanol (100 mL) and triethylamine (11.01 ml, 79 mmol) was cooled in an ice bath and benzyl chloroformate (7.30 ml, 51.3 mmol) was added, then the solution was allowed to warm to RT. Then chloroform was added and the solution was washed with water and processed normally. The crude residue was triturated with petroleum ether to give benzyl ((5R/S,6R/S)-6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)methylcarbamate (7.73 g, 24.99 mmol, 63.3% yield) as a white solid. 13C NMR (CDCl3) δ 157.3, 136.9, 128.9, 128.5, 128.5, 102.1, 69.1, 67.2, 64.6, 59.8, 46.4, 40.0, 25.2, 25.0.

後処理

  1. customAfter 2 days the solids and solvent were removed
  2. washthe solution was washed with water
  3. customThe crude residue was triturated with petroleum ether

出典と根拠

ORDレコード
ord-b3d16765aa874825b66ebb32a704d848
出典データセット
uspto-grants-2013_02
特許番号
US08383636B2

反応ノート

読み込み中…