1,3-Dibenzyl-4-hydroxypiperidine → 4-Hydroxy-3-benzylpiperidine

HRID 396328ノート

反応式

HRID 396328 の反応式
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[OH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 1

HCID 230037131,3-Dibenzyl-4-hydroxypiperidine

生成物 1

HCID 230036754-Hydroxy-3-benzylpiperidine

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒HCID 178418361HCID 178418361、化合物溶媒

実験手順

A mixture of 1,3-dibenzyl-4-hydroxypiperidine (1.7 g, 6.0 mmole) and 20% palladium hydroxide (0.3 g) in methanol (20 ml) was stirred in hydrogen atmosphere (1 atm.) for 12 hr at 35° C. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 4-hydroxy-3-benzylpiperidine as oil. Yield 1.0 g (91%), C12H17NO, m/z 192 (M+1) PMR (CDCl3): 1.66 (1H, m, H3), 1.94 (1H, m, H5), 2.26 (2H, m, H5, & OH, D2O exchangeable), 2.62 (1H, m, H2), 2.74 (1H, m, H6), 3.02 (1H, m, H2), 3.34 (1H, m, H6), 3.52 (1H, bs, NH, D2O exchangeable), 3.9 (1H, m, H4), 4.74 (2H, m, CH2-Ar), 7.28 (5H, m, ArH).

後処理

  1. filtrationCatalyst was filtered off
  2. washwashed with methanol, filtrate
  3. concentrationwas concentrated to dryness

出典と根拠

ORDレコード
ord-fbf4a62d9d524262b8f37191a528f44d
出典データセット
uspto-grants-2003_08
特許番号
US06608078B2

反応ノート

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