Water → (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol

Temperature

0 °C

Borane-dimethyl sulfide (0.63 ml, 6.3 mmol) was added to a solution of (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylcarboxylic acid (1.12 g, 3.13 mmol) in THF (30 ml) under stirring at 0° C. The reaction mixture was stirred at 50° C. for 1.5 hours. After the reaction mixture was cooled to 0° C., water (20 ml) was added thereto. The mixture was then extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (50/1) eluate fractions, the title compound (1.10 g, 100%) was obtained as a pale yellow oil.

1. stirringThe reaction mixture was stirred at 50° C. for 1.5 hours
2. temperatureAfter the reaction mixture was cooled to 0° C.
3. extractionThe mixture was then extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. distillationdistilled under reduced pressure
7. customto remove the solvent
8. customThe residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from chloroform/methanol (50/1) eluate fractions

ORD record

ord-a12a08bcadc54382aff4152850109a09

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2