Aluminium lithium hydride → Carbamic acid, [(1R)-1-(hydroxymethyl)-3-butenyl]-, 1,1-dimethylethyl ester

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Reaction Steps

A solution of compound 18f (9.5 g, 41.5 mmol) in THF (50 mL) was cooled in an ice bath under argon. To this mixture was added LAH (3.9 g, 104 mmol) portionwise, and then the ice bath was removed and the reaction mixture was allowed to stir at rt for 2 h and then quenched with water (30 mL). The aqueous layer was extracted with EA (3×50 mL). The combined extracts were washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC to give compound 18g (6.2 g, 75% yield) as yellow oil.

Provenance & Evidence