Hydrogen Peroxide → (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide

A solution of 0.105 g (0.634 mmol) of (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarbonitrile in 4.9 mL of dimethyl sulfoxide was placed in a 10 mL flask with a magnetic stir bar. After adding 0.60 mL of 35% hydrogen peroxide and 0.097 g (1.2 mmol) of 50% sodium hydroxide solutions the flask was capped and stirred at room temperature for 20 h. The reaction mixture was diluted with 10 mL of water, extracted twice with 10 mL of methylene chloride. The combined methylene chloride layers were back extracted with 3×20 mL of water, dried over magnesium sulfate, and concentrated in vacuo to provide an off-white solid that was further purified by column chromatography (silica gel, 75:25 hexane:ethyl acetate) to provide (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide.

1. customwas capped
2. extractionextracted twice with 10 mL of methylene chloride
3. extractionThe combined methylene chloride layers were back extracted with 3×20 mL of water
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customto provide an off-white solid
7. customthat was further purified by column chromatography (silica gel, 75:25 hexane:ethyl acetate)

ORD record

ord-d0a756228eda4eb486d1c59b908cab25

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426643B2