tert-butyl N-[(1S)-1-cyclopropyl-2-hydroxyethyl]carbamate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-2-cyclopropylacetate (5.35 g, 23.33 mmol) in Et2O (100 ml) was added LiBH4 (0.762 g, 35.0 mmol), followed by drop wise addition of methanol (1.420 ml, 35.0 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×100 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (4.16 g). LCMS m/z 224.1 (M+Na)+, Rt 0.62 min. The reaction mixture was then cooled to 0° C. quenched with HCl (1M) until pH=2 for aqueous layer The phases were separated the aqueous layer was extracted with DCM (3×100 mL) The organic was then dried (Na2SO4) concentrated under reduced pressure