Methanol → 4-(3-Hydroxymethylthiophen-2-yl)piperidine-1-carboxylic Acid t-Butyl Ester

HRID 41651ノート

反応式

HRID 41651 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[C:19](OC)=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[CH2:19][OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 887MethanolHCID 584428224-(3-Methoxycarbonylthiophen-2-yl)piperidine-1-carboxylic acid t-butyl ester

生成物 1

HCID 584428334-(3-Hydroxymethylthiophen-2-yl)piperidine-1-carboxylic Acid t-Butyl Ester収率 50.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-(3-methoxycarbonylthiophen-2-yl)piperidine-1-carboxylic acid t-butyl ester (3.8 g, 12 mmol, 1.0 eq.) in THF (70 mL) was degassed and purged with nitrogen (2×). Borane dimethyl sulfide complex (45 mL, 90 mmol, 110 eq.) was added at room temperature and the mixture was heated to reflux for 3 hours. The mixture was allowed to cool to room temperature and MeOH (20 mL) was slowly added. The mixture was then concentrated under vacuum. The addition of MeOH (20 mL) and concentrating was repeated two additional times. The crude material was applied onto a silica gel column and purified by chromatography with PE/EtOAc (10:1). The product was then purified by preparative HPLC to yield the title compound (1.8 g) as a white solid.

後処理

  1. custompurged with nitrogen (2×)
  2. additionBorane dimethyl sulfide complex (45 mL, 90 mmol, 110 eq.) was added at room temperature
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3 hours
  5. concentrationThe mixture was then concentrated under vacuum
  6. additionThe addition of MeOH (20 mL)
  7. concentrationconcentrating
  8. custompurified by chromatography with PE/EtOAc (10:1)
  9. customThe product was then purified by preparative HPLC

出典と根拠

ORDレコード
ord-bd76f08f064846afb8b81bb52de19af5
出典データセット
uspto-grants-2013_09
特許番号
US08530663B2

反応ノート

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