3-Methoxybenzylamine → HCID 68671093, compound

HRID 1784920Notes

Reaction equation

HRID 1784920 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([CH:16]1[CH2:18][O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH2:26]>CC(O)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH:26][CH2:18][CH:16]([OH:17])[CH:8]([NH:7][C:6](=[O:19])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 211563-MethoxybenzylamineHCID 4571240tert-Butyl (1-(oxiran-2-yl)-2-phenylethyl)carbamate

Product 1

HCID 68671093HCID 68671093, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of tert-butyl-(1-oxiranyl-2-phenylethyl)-carbamate (131.6 mg, 0.5 mmol), 3-methoxy-benzylamine (0.25 mL, 2 mmol) in 3 mL of 2-propanol was heated to reflux for 12 h to afford tert-butyl 4-(3-methoxybenzylamino)-3-hydroxy-1-phenylbutan-2-ylcarba-mate. The solvent was evaporated and the crude product was purified by silica gel flash column chromatography (5-10% MeOH in CHCl3) to give 4 in 77% yield (154 mg) as a colorless solid.

Workup

  1. temperatureto reflux for 12 h

Sources & evidence

ORD record
ord-e9b67d4b36004ece928ef24a89ab9278
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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