HCID 57671244, compound → methyl (1R,2S)-2-aminocyclopentane-1-carboxylate

HRID 731297Notes

Reaction equation

C(OC([NH:11][C@H:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]([O:19][CH3:20])=[O:18])=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of methyl (1R,2S)-2-{[(benzyloxy)carbonyl]amino}cyclopentanecarboxylate (6.5 g, 23.5 mmol) in ethyl acetate (200 mL), 5% Palladium on carbon (1.3 g, 20% w/w) was added. The flask was degassed and backfilled with hydrogen gas via balloon. The mixture was stirred at 25° C. for 1.5 h, passed through a plug of Celite and rinsed with ethyl acetate. The filtrate was concentrated in vacuo to afford the desired product, methyl (1R,2S)-2-aminocyclopentanecarboxylate (4.30 g, 30.05 mmol, quantitative), as a clear oil. 1H NMR (400 MHz, CDCl3) δ: 1.57 (2H, m), 1.90 (3H, m), 2.05 (1H, m), 2.81 (1H, m), 3.61 (1H, m), 3.72 (3H, s).

Workup

customThe flask was degassed
washrinsed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-3620ad633eab414cb6b3501c59c4a008
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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