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

HRID 1963934Notes

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-c2f806b04a4a4c1ab3bd4929f78bd802
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415381B2

Reaction notes

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