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

HRID 446943노트

반응식

HRID 446943 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2c0ca4a7406948369a3cb1b46451d050
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481541B2

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