Water → tert-butyl N-[(1R,2S)-2-(hydroxymethyl)cyclopentyl]carbamate

To a well stirred suspension of 0.94 g (24.7 mmol, 2 equiv.) of LiAlH4 in 30 ml of THF at 0° C. was added dropwise at 0° C. a solution of (1S,2R)-methyl 2-(tert-butoxycarbonylamino)-cyclopentanecarboxylate (CAS: 592503-55-4) (3.0 g, 12.3 mmol) (gas evolution, lightly exotherm). After 15 minutes at 0° C. the reaction mixture was allowed to warm up to room temperature and was stirred for 2 h. The mixture was cooled to 0° C. and water was added dropwise. The precipitated inorganic salts were filtered through Celite and were washed with ethyl acetate. The filtrate was evaporated and the residue was purified by column chromatography on silica gel eluting with a 0% to 50% ethyl acetate in heptane gradient to yield 1.99 g (75%) of the title compound as a crystalline white solid which was directly used in the next step.

1. stirringwas stirred for 2 h
2. temperatureThe mixture was cooled to 0° C.
3. filtrationThe precipitated inorganic salts were filtered through Celite
4. washwere washed with ethyl acetate
5. customThe filtrate was evaporated
6. customthe residue was purified by column chromatography on silica gel eluting with a 0% to 50% ethyl acetate in heptane gradient

ORD record

ord-3769a159cf1b4e77b4e347293a6879dd

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221802B2