Water → (R)-tert-Butyl(1-methyl-2-oxopiperidin-3-yl)carbamate

HRID 446943ノート

反応式

HRID 446943 の反応式
[O:1]=[C:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].I[CH3:19].O>CN(C)C=O>[CH3:19][N:3]1[CH2:4][CH2:5][CH2:6][C@@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[C:2]1=[O:1]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 45092193(R)-tert-Butyl (2-oxopiperidin-3-yl)carbamate

生成物 1

HCID 67388684(R)-tert-Butyl(1-methyl-2-oxopiperidin-3-yl)carbamate収率 45.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (R)-tert-butyl 2-oxopiperidin-3-ylcarbamate (642 mg, 3.00 mmol) in N,N-dimethylformamide (3 mL) at room temperature was added sodium hydride (132 mg, 3.3 mmol). The reaction mixture stirred for 30 min, then iodomethane (206 μL, 3.3 mmol) was added and stirring was continued for 1 h. The reaction mixture was poured into water (50 mL) and extracted with EtOAc (100 mL), using a continuous extractor apparatus overnight. The organic extract was evaporated to dryness under vacuum and the crude residue was purified by SiO2 chromatography (23 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3) to give 310 mg (45%) of (R)-tert-butyl 1-methyl-2-oxopiperidin-3-ylcarbamate as a colorless viscous oil.

後処理

  1. stirringstirring
  2. waitwas continued for 1 h
  3. extractionextracted with EtOAc (100 mL)
  4. customa continuous extractor apparatus overnight
  5. extractionThe organic extract
  6. customwas evaporated to dryness under vacuum
  7. customthe crude residue was purified by SiO2 chromatography (23 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3)

出典と根拠

ORDレコード
ord-2c0ca4a7406948369a3cb1b46451d050
出典データセット
uspto-grants-2013_07
特許番号
US08481541B2

反応ノート

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