Triethylamine → (1,1-Dimethyl-4-nitro-but-3-enyl)-carbamic acid tert-butyl ester

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Reaction Steps

To (3-Hydroxy-1,1-dimethyl-4-nitro-butyl)-carbamic acid tert-butyl ester (2.00 g, 7.6 mmol) and triethylamine (2.73 g, 27.0 mmol) in 50 mL CH2Cl2 at −10° C. was added dropwise over 5 min. methanesulfonyl chloride. The mixture was warmed to rt for 1 h, and then was diluted with water and extracted with CH2Cl2 (3×30 mL). The extracts were washed sequentially with 1% HCl, water and brine and were dried over MgSO4 and concentrated. Silica gel chromatography (10:1 hexane/EtOAc) gave 1.07 g (60%) of a colorless oil: 1H NMR (300 MHz, CD3OD) d 7.1–7.4 (comp, 2H), 2.72 (d, 2H, J 7.5 Hz), 1.46(s, 9H), 1.31 (s, 6H).

Provenance & Evidence