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

HRID 446506ノート

反応式

HRID 446506 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-03e818db257547fd8fa7302833afd43c
出典データセット
uspto-grants-2013_07
特許番号
US08476253B2

反応ノート

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