Water → Methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamate

HRID 2068997

反応式

HRID 2068997 の反応式
[BH4-].[Na+].[Br-].[CH2:4]([N+:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([NH:18][C:19]([O:21][CH3:22])=[O:20])[CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CO>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([CH3:17])=[C:13]([NH:18][C:19](=[O:20])[O:21][CH3:22])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 667702031-Benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide

生成物 1

HCID 58526548Methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamate収率 66.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (4.4 g, 116 mmol, 1.20 equiv.) was added in several batches to a solution of 1-benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide (35 g, 104 mmol, 1.00 equiv.) in methanol (300 mL). The resulting solution was stirred at ambient temperature for about 16 hours, and then water (200 mL) was added. After concentrating the mixture in vacuo, standard extractive workup with ether (3×200 mL) gave a crude residue that was then purified by silica gel column chromatography (dichloromethane/methanol (20:1)) to afford the title product as a yellow solid (18 g; yield=66%). LC-MS: m/z=261 (M+H)+.

後処理

  1. concentrationAfter concentrating the mixture in vacuo, standard extractive workup with ether (3×200 mL)
  2. customgave a crude residue that
  3. customwas then purified by silica gel column chromatography (dichloromethane/methanol (20:1))

出典と根拠

ORDレコード
ord-4b3621c424864c319cffa80e57599381
出典データセット
uspto-grants-2012_10
特許番号
US08299084B2

関連ノート

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