Ammonium Chloride → 1,1-Dimethylethyl (3-hydroxypentyl)methylcarbamate

HRID 1243607Notes

Reaction equation

[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=[O:13])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH2:14]([Mg]Br)[CH3:15].[Cl-].[NH4+]>O1CCCC1>[OH:13][CH:12]([CH2:14][CH3:15])[CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

N-Methyl-(3-oxopropyl)carbamic acid, 1,1-dimethylethyl ester (2.00 g, 10.7 mmol) was dissolved in tetrahydrofuran (20 ml) under nitrogen and cooled to 0° C. with stirring. To the resulting solution was added ethylmagnesium bromide and the mixture stirred at 0° C. for a further 30 minutes and then allowed to warm to room temperature with stirring over 20 h. The mixture was then poured into saturated ammonium chloride solution and then extracted with diethyl ether three times. The combined organic fractions were then washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue eluted down a flash chromatography column using 40% diethyl ether/isohexane as eluent to give 1.70 g (65%) of the title compound as an oil.

Workup

stirringthe mixture stirred at 0° C. for a further 30 minutes
temperatureto warm to room temperature
stirringwith stirring over 20 h
extractionextracted with diethyl ether three times
washThe combined organic fractions were then washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
washthe residue eluted down a flash chromatography column

Sources & evidence

ORD record: ord-17b108ecb9f6496b9db4695f5bd17b48
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119109B2

Reaction notes

Loading…