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

HRID 1377769ノート

反応式

HRID 1377769 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-8c73535a532f4d5d8fce8ec1579f0baf
出典データセット
uspto-grants-1997_09
特許番号
US05665754

反応ノート

読み込み中…