Diisopropylamine → HCID 68743244, compound

A solution of lithium diisopropylamide prepared from diisopropylamine (6.50 mL) and butyllithium (29.0 mL of 1.6M solution in hexanes) in THF (105 mL) was treated dropwise with 2-(cyclohexyl-methyl)-γ-butyrolactone (6.96 g) at −78° C. The reaction mixture was stirred at the same temperature for additional 30 min and then treated dropwise with chloromethyl ethyl ether (5.05 g). Upon completion of the addition, the mixture was allowed to slowly warm-up to room temperature and stirred at this temperature overnight. After that, the mixture was quenched by pouring onto a mixture of ice and 10% aqueous phosphoric acid. The formed organic phase was separated and the aqueous phase was extracted with toluene. The combined organic phases were washed with water, dried over potassium sulfate, filtered, concentrated on a rotary evaporator and purified by column chromatography (silica gel, eluent-hexane) to give 5.90 g (64%) of the title compound.

1. additionUpon completion of the addition
2. stirringstirred at this temperature overnight
3. customAfter that, the mixture was quenched
4. additionby pouring onto a mixture of ice and 10% aqueous phosphoric acid
5. customThe formed organic phase was separated
6. extractionthe aqueous phase was extracted with toluene
7. washThe combined organic phases were washed with water
8. dry with materialdried over potassium sulfate
9. filtrationfiltered
10. concentrationconcentrated on a rotary evaporator
11. custompurified by column chromatography (silica gel, eluent-hexane)

ORD record

ord-52da25c55cf6475287b7e8a38face0c8

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674741B2