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

HRID 1858833노트

반응식

HRID 1858833 반응식
C([O:8][C:9]1[CH:10]=[N:11][C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]2[OH:28])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:28][CH:16]1[CH:15]([C:12]2[N:13]=[CH:14][C:9]([OH:8])=[CH:10][N:11]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1

참가 물질

4

반응물 1

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

생성물 1

HCID 54564538tert-butyl (3RS,4RS)-3-hydroxy-4-(5-hydroxy-pyrimidin-2-yl)-piperidine-1-carboxylate수율 93.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 110 mg (0.29 mmol) of tert-butyl (3RS,4RS)-4-(5-benzyloxy-pyrimidin-2-yl)-3-hydroxy-piperidine-1-carboxylate in 5 ml of methanol was treated with 20 mg of 5% palladium-charcoal and hydrogenated at room temperature for 12 hours. For the working-up, the catalyst was filtered off and washed with 20 ml of methanol. The methanol solution was evaporated under reduced pressure and the resulting oil was crystallized by the addition of ether. There were obtained 80 mg (93% of theory) of tert-butyl (3RS,4RS)-3-hydroxy-4-(5-hydroxy-pyrimidin-2-yl)-piperidine-1-carboxylate in the form of colourless, slightly delequesent crystals; MS: 296 (M+H)+.

후처리

  1. filtrationthe catalyst was filtered off
  2. washwashed with 20 ml of methanol
  3. customThe methanol solution was evaporated under reduced pressure
  4. customthe resulting oil was crystallized by the addition of ether

출처 및 근거

ORD 기록
ord-6e7dea4100b844c7b549941587cade00
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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