3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidine → tert-Butyl methyl{1-[(3R)-pyrrolidin-3-yl]cyclopropyl}carbamate

HRID 600900Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)amino]cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidine (7.19 g, 20.9 mmol) was dissolved in ethanol (78 ml), and after adding a 10% palladium carbon catalyst (water content: 50%; 3.9 g), it was stirred at 40° C. for 4 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, 4.38 g (quantitative) of the title compound was obtained in the form of a colorless syrup. The 1H-NMR data and the TLC Rf value of this resulting compound agreed with the data indicated previously.

Workup

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

Sources & evidence

ORD record: ord-7c4cda77748448dfbd2ba69c18e7656e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902226B2

Reaction notes

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