Methyl chloroformate → HCID 20694319, compound

HRID 380506Notes

Reaction equation

HRID 380506 reaction equation
C([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C@H:10]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH2:9]1)C1C=CC=CC=1.[CH3:32][O:33][C:34](Cl)=[O:35]>C1COCC1>[CH3:32][O:33][C:34]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C@H:10]([CH2:18][N:19]2[CH2:20][CH2:21][CH:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:23][CH2:24]2)[CH2:9]1)=[O:35]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 9824260HCID 9824260, compound

Product 1

HCID 20694319HCID 20694319, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.35 g (10 mmol) of 1-benzyl-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(R)-(3-thienyl)pyrrolidine in 20 mL of THF at 0° C. was added 3.7 mL (26 mmol) of methylchloroformate and the reaction mixture was warmed to rt and stirred for 2 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, acetone: hexanes, 1:3) to give 3.5 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, acetone: hexanes, 1:3)

Sources & evidence

ORD record
ord-542e2916c9c4488ba813023c99198a51
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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