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

HRID 45584ノート

反応式

HRID 45584 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8c00a6bebe7d4434a005fa03dc9abcc2
出典データセット
uspto-grants-2013_09
特許番号
US08541585B2

反応ノート

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