1-(2,2,2,-Trichloroethoxycarbonyl)-3-(RS)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine → Methyl 4-(thiophen-3-yl)pyrrolidine-3-carboxylate

HRID 380475Notes

Reaction equation

ClC(Cl)(Cl)COC([N:7]1[CH2:11][CH:10]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:9]([C:17]([O:19][CH3:20])=[O:18])[CH2:8]1)=O>C(O)(=O)C.[Zn]>[NH3:7].[C:17]([CH:9]1[CH:10]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH2:11][NH:7][CH2:8]1)([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 1.1 g (2.9 mmol) of 1-(2,2,2,-trichloroethoxycarbonyl)-3-(SR)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine in 30 mL of acetic acid at 40° C. was slowly added 0.5 g (7.6 mmol) of Zn powder and the reaction mixture was stirred a further 4 h at 40° C. The reaction mixture was filtered to remove the solid and the filter was washed with MeOH. The organic fraction was concentrated and the residue was purified by chomatography. (silica, CH2Cl9: MeOH: NH3 (2M in MeOH),100:4:2) to give 0.61 g of the title compound. 1H NMR (CDCl3) δ2.92 (m, 1H). 3.02 (m, 1H), 3.29 (m, 2H), 3.48-3.62 (m, 2H), 3.72 (s, 3H), 6.99 (d, 1H, J=5 HZ), 7.05 (s, 1H), 7.31 (m, 1H);

Workup

customat 40° C.
filtrationThe reaction mixture was filtered
customto remove the solid
washthe filter was washed with MeOH
concentrationThe organic fraction was concentrated
customthe residue was purified by chomatography

Sources & evidence

ORD record: ord-969141ba1a854b808242cb2b851d173f
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303593B1

Reaction notes

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