Methyl chloroformate → HCID 44302318, compound

HRID 1377763Notes

Reaction equation

HRID 1377763 reaction equation
[C:1]([CH:3]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)[CH2:6][N:5](CC2C=CC=CC=2)[CH2:4]1)#[N:2].Cl[C:30]([O:32][CH3:33])=[O:31]>CC#N>[C:1]([C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)[CH2:6][N:5]([C:30]([O:32][CH3:33])=[O:31])[CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 22915229HCID 22915229, compound

Product 1

HCID 44302318HCID 44302318, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-cyano-4-(3-cyclopentoxy-4-methoxyphenyl)-1-(phenylmethyl)pyrrolidine (300 mg, 0.79 mmol) in 2 mL of CH3CN in a thick-walled glass sealable tube was added methyl chloroformate (300 mg, 3.19 mmol). The tube was sealed and the resulting solution was heated to 80° C. for 12 hr. After cooling to room temperature, the solution was concentrated. Silica gel chromatography of the residue (2:1, hexanes:ethyl acetate) provided trans-3-cyano-4-(3-cyclopentoxy-4-methoxyphenyl)-1-(methoxycarbonyl)pyrrolidine as a white solid (233 mg, 85%), m.p. 101°-104° C. Anal. Calcd for C19H24N2O4 : C, 66.26; H, 7.02; N, 8.13. Found: C, 66.14; H, 7.06; N, 8.10.

Workup

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

Sources & evidence

ORD record
ord-217e29c368134e07966fc547e5f20473
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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