Methanol → Benzyl {3-[{[5-(hydroxymethyl)pyridin-2-yl]carbonyl}(methyl)amino]propyl}methylcarbamate

HRID 446506노트

반응식

HRID 446506 반응식
[CH2:1]([O:8][C:9]([N:11]([CH3:28])[CH2:12][CH2:13][CH2:14][N:15]([CH3:27])[C:16]([C:18]1[N:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=1)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.CO>O1CCCC1>[OH:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]([N:15]([CH3:27])[CH2:14][CH2:13][CH2:12][N:11]([CH3:28])[C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:17])=[N:23][CH:22]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 666715476-[(3-{[(Benzyloxy)carbonyl](methyl)amino}propyl)(methyl)carbamoyl]pyridine-3-carboxylic acid

생성물 1

HCID 66671755Benzyl {3-[{[5-(hydroxymethyl)pyridin-2-yl]carbonyl}(methyl)amino]propyl}methylcarbamate수율 37%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The compound (350 mg, 0.908 mmol) obtained in Example 5b was dissolved in tetrahydrofuran (4 mL), a borane-tetrahydrofuran complex (1.0 M tetrahydrofuran solution; 3.18 mL, 3.18 mmol) was added under ice cooling, and then the mixture was stirred at room temperature for 45 minutes. Methanol (1 mL) was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=100:0→20:1, v/v) to give the title compound (124 mg; yield, 37%) as a colorless oily substance.

후처리

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate

출처 및 근거

ORD 기록
ord-03e818db257547fd8fa7302833afd43c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

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