3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(ethyl)Amino]Cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidine → 3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(ethyl)amino]cyclopropyl]pyrrolidine

HRID 600903Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:11]1([C@@H:14]2[CH2:18][CH2:17][N:16]([C@H](C3C=CC=CC=3)C)[CH2:15]2)[CH2:13][CH2:12]1)[CH2:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([N:8]([C:11]1([C@@H:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)[CH2:13][CH2:12]1)[CH2:9][CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(ethyl)amino]cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidine (3.01 g, 8.40 mmol) was dissolved in ethanol (120 ml), and after adding a 10% palladium carbon catalyst (water content: 50%; 3.0 g), it was stirred at 40° C. for 5 hours under a hydrogen atmosphere at atmospheric pressure. After performing filtration through cellite (ethanol washing), the filtrate was concentrated under a reduced pressure. As a result, 2.16 g (quantitative) of the title compound was obtained in the form of a colorless syrup.

Workup

filtrationfiltration through cellite (ethanol washing)
concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record: ord-fe82bc07047d40818c3561c6ab4b6421
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902226B2

Reaction notes

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