Lithium borohydride → HCID 117702498, compound

Participants

Reaction Steps

To a solution of methyl 5-(tert-butoxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (7.8 g, 27.6 mmol) in THF (65 mL) was added LiBH4 (2.0 M in THF, 28 mL, 56.0 mmol) dropwise at 0° C. under N2. The solution was warmed up to room temperature gradually and stirred overnight. The reaction mixture was quenched with Sat. NH4Cl and extracted with ethyl acetate (3×150 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 7.0 g (90%) of the crude title compound, tert-Butyl 5-(hydroxymethyl)bicyclo[3.2.1]octan-1-ylcarbamate, as colorless oil, which was used in the next step without further purification. ESI-MS m/z: 200 (M-55)+.

Provenance & Evidence