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

HRID 2068997

반응식

HRID 2068997 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+.

후처리

  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))

출처 및 근거

ORD 기록
ord-4b3621c424864c319cffa80e57599381
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299084B2

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