Sodium Methoxide → tert-butyl (3RS,4RS)-4-(5-benzyloxy-pyrimidin-2-yl)-3-hydroxy-piperidine-1-carboxylate

HRID 1005215노트

반응식

HRID 1005215 반응식
C(O)(=O)C.[C:5]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[OH:21])(=[NH:7])[NH2:6].C[O-].[Na+].[CH2:25]([O:32][C:33](=[CH:36]N(C)C)[CH:34]=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[CH2:25]([O:32][C:33]1[CH:34]=[N:7][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:10][CH:9]2[OH:21])=[N:6][CH:36]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 545210022-Benzyloxy-3-(dimethylamino)acroleinHCID 86604511tert-butyl (3RS,4RS)-4-carbamimidoyl-3-hydroxy-piperidine-1-carboxylate acetate

생성물 1

HCID 54513866tert-butyl (3RS,4RS)-4-(5-benzyloxy-pyrimidin-2-yl)-3-hydroxy-piperidine-1-carboxylate수율 27.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 372 mg (1 mmol) of tert-butyl (3RS,4RS)-4-carbamimidoyl-3-hydroxy-piperidine-1-carboxylate acetate in 10 ml of methanol was treated with 1 ml of 1N sodium methylate solution and stirred at room temperature. Subsequently, 205 mg (1 mmol) of 2-benzyloxy-3-dimethylamino-acrolein (EPA 0 477 901) were added thereto and the solution was heated to reflux for 18 hours. For the working-up, the reaction mixture was evaporated under reduced pressure and the residue was taken up in 20 ml of methylene chloride and washed with 5 ml of water. The organic phase was separated, dried over sodium sulphate and finally evaporated under reduced pressure. For purification, the residue was chromatographed on silica gel using a 1:4 mixture of methylene chloride and ethyl acetate as the eluent. There were obtained 106 mg (27% of theory) of tert-butyl (3RS,4RS)-4-(5-benzyloxy-pyrimidin-2-yl)-3-hydroxy-piperidine-1-carboxylate as a colourless oil; MS: 386 (M+H)+.

후처리

  1. temperaturethe solution was heated
  2. temperatureto reflux for 18 hours
  3. customthe reaction mixture was evaporated under reduced pressure
  4. washwashed with 5 ml of water
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulphate
  7. customfinally evaporated under reduced pressure
  8. customFor purification
  9. customthe residue was chromatographed on silica gel using
  10. additiona 1:4 mixture of methylene chloride and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-e2304e2d2fda451f82de7f43d9469d9c
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051712

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