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 1005216ノート

反応式

HRID 1005216 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-25f1aa4243dc4bafbec1915f33666766
出典データセット
uspto-grants-2000_04
特許番号
US06051712

反応ノート

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