Chloroform → HCID 131730260, 화합물

HRID 390086노트

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HRID 390086 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 131730260HCID 131730260, 화합물수율 63.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b3d16765aa874825b66ebb32a704d848
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383636B2

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