Benzylamine → Methyl 3-methyl-3-[(phenylmethyl)amino]butanoate

HRID 1366611Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:16])=[CH:11][C:12]([O:14][CH3:15])=[O:13]>CO.O>[CH3:9][C:10]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of benzylamine (10.0 mL, 91.6 mmol) in 95% MeOH-water (180 mL) was added methyl 3-methyl-2-butenoate (12.3 mL, 100.8 mmol). The solution was heated at 55° C. and stirred for 2 weeks. The solution was then cooled to room temperature, concentrated in vacuo, and the residue purified by gradient silica gel chromatography (0% to 100% EtOAc in hexanes; 1% Et3N) to provide methyl 3-methyl-3-[(phenylmethyl)amino]butanoate (5.5893 g, 28%) as a pale yellow oil. LCMS: (M+H)+: 222.1.

Workup

temperatureThe solution was then cooled to room temperature
concentrationconcentrated in vacuo
customthe residue purified by gradient silica gel chromatography (0% to 100% EtOAc in hexanes; 1% Et3N)

Sources & evidence

ORD record: ord-88251ba43d60432e9e625aacf9f1c6fd
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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