Methyl chloroformate → HCID 10338622, compound

HRID 1377764Notes

Reaction equation

HRID 1377764 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([CH3:22])=[O:21])[CH2:18][N:17](CC4C=CC=CC=4)[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:31]([O:33][CH3:34])=[O:32]>ClC(Cl)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([CH3:22])=[O:21])[CH2:18][N:17]([C:31]([O:33][CH3:34])=[O:32])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 70093783HCID 70093783, compound

Product 1

HCID 10338622HCID 10338622, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methylcarbonyl-1-(phenylmethyl)pyrrolidine (703 mg, 1.78 mmol) in 3.5 mL of dichloroethane in a thick-walled glass sealable tube was added methyl chloroformate (336 mg, 3.56 mmol). The tube was sealed and the resulting solution was heated to 80° C. for 8 hr. After cooling to room temperature, the solution was concentrated. Silica gel chromatography of the residue (6:3:1, hexanes:ethyl acetate:CH2Cl2) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-1-methoxycarbonyl-4-(methylcarbonyl)pyrrolidine as a viscous oil (350 mg, 54%). Anal. Calcd for C20H27NO5 : C, 66.46; H, 7.53; N, 3.88. Found: C, 66.24; H, 7.60; N, 3.79.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-28a6e6b5b16f467aa6364fb9a2446c37
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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