3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidine → (R)-t-Butyl (1-(pyrrolidin-3-yl)cyclopropyl)carbamate

HRID 600895Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1([C@@H:12]2[CH2:16][CH2:15][N:14]([C@H](C3C=CC=CC=3)C)[CH2:13]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][C:9]1([C@@H:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH2:10][CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidine (270 mg, 0.817 mmol) was dissolved in ethanol (15 ml), and after adding a 10% palladium carbon catalyst (water content: 52.0%; 270 mg), it was stirred at 40° C. for 3 hours under a hydrogen atmosphere at atmospheric pressure. After removing the catalyst by filtering (ethanol washing), the filtrate was concentrated under a reduced pressure, and as a result, 185 mg (quantitative) of the title compound was obtained in the form of a colorless syrup.

Workup

customAfter removing the catalyst
filtrationby filtering (ethanol washing)
concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record: ord-d386fa7646134efa819e06ac83ebf50a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902226B2

Reaction notes

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