Triethylamine → Tert-butyl 5-oxo-1,4-oxazepane-4-carboxylate

HRID 45584Notes

Reaction equation

HRID 45584 reaction equation
[O:1]1[CH2:7][CH2:6][C:5](=[O:8])[NH:4][CH2:3][CH2:2]1.[C:9]([O:13][C:14](=O)[O:15]C(C)(C)C)([CH3:12])([CH3:11])[CH3:10].CN(C1C=CC=CN=1)C.C(N(CC)CC)C>ClCCl.O>[O:8]=[C:5]1[CH2:6][CH2:7][O:1][CH2:2][CH2:3][N:4]1[C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 70230201,4-Oxazepan-5-oneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 68190041Tert-butyl 5-oxo-1,4-oxazepane-4-carboxylateYield 465%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,4-oxazepan-5-one (6.9 g, 60.0 mmol) in dichloromethane (120.0 mL) were added di-tert-butylcarbonate (1.75 g, 8.00 mmol) and dimethylaminopyridine (7.90 g, 65.0 mmol), and triethylamine (12.5 mL, 90.0 mmol) was added dropwise. After stirring for 16 hours at room temperature, to the mixture was added water, and the aqueous layer was extracted with chloroform. The organic layer was washed with saturated aqueous solution of ammonium chloride and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate=90/10 to 0/100) to give the title compound (7.30 g, 37.2 mmol, 62%).

Workup

  1. additionwas added dropwise
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe organic layer was washed with saturated aqueous solution of ammonium chloride and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified with silica gel column (hexane/ethyl acetate=90/10 to 0/100)

Sources & evidence

ORD record
ord-8c00a6bebe7d4434a005fa03dc9abcc2
Source dataset
uspto-grants-2013_09
Patent number
US08541585B2

Reaction notes

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