Benzyl chloroformate → Benzyl (2-amino-2-methylpropyl)carbamate

HRID 1756542Notes

Reaction equation

[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[NH2:6][C:3]([CH3:5])([CH3:4])[CH2:2][NH:1][C:15](=[O:16])[O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To a 65 g sample of 1,2-diamino-2-methylpropane dissolved in 650 mL of toluene cooled to -5° C. was added dropwise over 45 minutes a toluene solution (200 mL) of benzylchloroformate (52 g, 1.18 mmol). The reaction was warmed to room temperature and stirred for 2 hours before it was filtered and the filtrate was stripped of all solvent under reduced pressure. The residue, dissolved in CH2Cl2 (100 mL), was filtered and the filtrate again was stripped of all solvent to produce the title compound (54 g) as a viscous oil.

Workup

temperatureThe reaction was warmed to room temperature
filtrationwas filtered
dissolutionThe residue, dissolved in CH2Cl2 (100 mL)
filtrationwas filtered

Sources & evidence

ORD record: ord-ebf315fd91b542f18c3c127ce441f409
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05441950

Reaction notes

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