Cyanogen Bromide → trans-1-Cyano-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

HRID 1377769Notes

Reaction equation

HRID 1377769 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[N:30]#[C:31]Br>CC#N.O.C(OCC)(=O)C>[C:31]([N:17]1[CH2:18][C@@H:19]([C:20]([O:22][CH3:23])=[O:21])[C@H:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[CH2:16]1)#[N:30]

Participants

7

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 70093357trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

Product 1

HCID 44391478trans-1-Cyano-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidineYield 51.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (300 mg, 0.94 mmol) and K2CO3 (195 mg, 1.5 mmol) in 5 mL of CH3CN at 0° C. was added cyanogen bromide (120 mg, 1.13 mmol). The solution was stirred for 24 hr, diluted with H2O and ethyl acetate, and washed with brine. The combined organic layers were dried over MgSO4, filtered and concentrated to an oil. Silica gel chromatography (3:1, hexanes:ethyl acetate) provided trans-1-cyano-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine as a white solid (166 mg, 51%).m.p. 78°-80° C. Anal. Calcd for C19H24N2O4 : C, 66.26; H, 7.02; N, 8.13. Found: C, 66.30; H, 7.04; N, 8.15.

Workup

  1. washwashed with brine
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-8c73535a532f4d5d8fce8ec1579f0baf
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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