Sodium borohydride → tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

HRID 1623373Notes

Reaction equation

[O:1]=[C:2]1[C@@H:7]2[CH2:8][C@@H:4]([CH2:5][CH2:6]2)[N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[BH4-].[Na+]>CO>[OH:1][CH2:2][C@H:7]1[CH2:6][CH2:5][C@@H:4]([NH:3][C:9](=[O:10])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

(1R,4S)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate (2.99 g, 14.15 mmol) was dissolved in MeOH (40 ml) and cooled to 0° C. Sodium Borohydride (1.071 g, 28.3 mmol) was added and the reaction was stirred at 0° C. for 1 hr, and the reaction progress was followed by LCMS. MeOH was removed and the resulting residue was partitioned between EtOAc (250 mL) and H2O (250 mL). The organic layer was washed with brine (250 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by column chromatography, 50-100% EtOAc in heptane to yield tert-butyl (1R,3S)-3-(hydroxymethyl)cyclopentylcarbamate (2.92 g, 13.56 mmol) as a white solid. LCMS (m/z): 160.2 (M-tBu), retention time=0.65 min.

Workup

customMeOH was removed
customthe resulting residue was partitioned between EtOAc (250 mL) and H2O (250 mL)
washThe organic layer was washed with brine (250 mL)
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude material was purified by column chromatography, 50-100% EtOAc in heptane

Sources & evidence

ORD record: ord-a4f1aeae3eb94480a57f2c0c6a52a9b3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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