Chloroform → HCID 131730260, compound

HRID 390086Notes

Reaction equation

HRID 390086 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 131730260HCID 131730260, compoundYield 63.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b3d16765aa874825b66ebb32a704d848
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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