Lithium hydroxide, monohydrate → 2-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Participants

Reaction Steps

To a mixture of (3R)-2-tert-butyl 3-ethyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate (D26) (diastereoisomer mixture) (3.4 g, 13.3 mmol) in dioxane (15 ml) and water (15 ml), LiOH H2O (2.2 g, 53 mmol). The mixture was stirret at RT for 18 h. Dioxane was evaporated off and water was washed with Et2O (2×40 ml) then the pH was adjusted to ˜4 by addition of citric acid and the resulting aqueous phase was extacted with DCM (200 ml), washed with water (20 ml), dried over Na2SO4 and evaporated in vacuo to afford the title compound (D27) (2.75 g) as diastereoisomer mixture with syn-anti ratio 10/2.

Provenance & Evidence