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

HRID 446506Notes

Reaction equation

HRID 446506 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-03e818db257547fd8fa7302833afd43c
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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