Benzyl chloroformate → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethoxycarbonyl)pyrrolidine

HRID 1377770ノート

反応式

HRID 1377770 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][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:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>C(O)=O.CO.C(Cl)Cl.CN(C1C=CN=CC=1)C.[Pd]>[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][N:17]([C:32]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

8

反応物 2

HCID 10387Benzyl chloroformateHCID 70091886trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine

生成物 1

HCID 44302345trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethoxycarbonyl)pyrrolidine収率 40%

試薬・触媒・溶媒 5

HCID 142844-(Dimethylamino)pyridine触媒HCID 23938Palladium触媒HCID 284Formic Acid溶媒HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine (3.1 g, 7.5 mmol) was dissolved in 50 mL of 4% HCO2H:methanol. While stirring at room temperature, 10% Pd/C (400 mg) was added in small portions. After 16 hrs the reaction was diluted with methanol. Filtration through Celite followed by concentration under reduced pressure yielded a yellow oil residue. This residue was dissolved in CH2Cl2 and DMAP (1.19 g, 9.75 mmol) and benzyl chloroformate (1.5 g, 8.2 mmol) were added. The resulting solution was stirred at room temperature. When reaction was judged complete by TLC analysis the mixture was partitioned between CH2Cl2 and 1M H3PO4. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, dried (MgSO4), filtered, and concentrated under reduced pressure to afford a pale oil. Chromatography on silica gel (3:2, hexanes:ethyl acetate) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethoxycarbonyl)pyrrolidine as a white solid (1.34 g, 40%). m.p. 85° C. Anal. Calcd for C26H31NO6 : C, 68.86; H, 6.89; N, 3.09. Found: C, 68.81; H, 6.94; N, 2.99.

後処理

  1. filtrationFiltration through Celite
  2. concentrationfollowed by concentration under reduced pressure
  3. customyielded a yellow oil residue
  4. stirringThe resulting solution was stirred at room temperature
  5. customWhen reaction
  6. customwas partitioned between CH2Cl2 and 1M H3PO4
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto afford a pale oil

出典と根拠

ORDレコード
ord-8a25bf0b489047ca8793c1c9d43cbbc2
出典データセット
uspto-grants-1997_09
特許番号
US05665754

反応ノート

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