2,2,2-Trichloroethyl chloroformate → 1-(2,2,2,-Trichloroethoxycarbonyl)-3-(RS)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine

HRID 380474Notes

Reaction equation

HRID 380474 reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:10]([C:18]([O:20][CH3:21])=[O:19])[CH2:9]1)C1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][C:27]([Cl:30])([Cl:29])[Cl:28])=[O:24]>CC#N>[Cl:28][C:27]([Cl:30])([Cl:29])[CH2:26][O:25][C:23]([N:8]1[CH2:12][CH:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:10]([C:18]([O:20][CH3:21])=[O:19])[CH2:9]1)=[O:24]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 69212355Methyl 1-benzyl-4-(thiophen-3-yl)pyrrolidine-3-carboxylate

Product 1

HCID 183649201-(2,2,2,-Trichloroethoxycarbonyl)-3-(RS)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidineYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.02 g (3.38 mmol) of 1-benzyl-3-(SR)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine (Example 1) and 0.51 mL (3.72 mmol) of 2,2,2-trichloroethyl chloroformate in 15 mL of CH3CN was stirred at rt for 1.5 h. The reaction mixture was concentrated and the residue was purified by chomatography (silica, hexanes, ethyl acetate, 6:1) to give 1.1 g of the title compound. 1H NMR (CDCl3) δ3.21 (m, 1H), 3.58 (m, 1H), 3.716, 3.723 (s, 3H), 4.81 (m, 2H), 7.00 (m, 1H), 7.12 (s, 1H), 7.33 (m, 1H);

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chomatography (silica, hexanes, ethyl acetate, 6:1)

Sources & evidence

ORD record
ord-3c423efcc3ad4e10af088db8a1fd4800
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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