Trifluoroacetic acid → Methyl 1-benzyl-4-cyclopropylpyrrolidine-3-carboxylate

HRID 1162723ノート

反応式

HRID 1162723 の反応式
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19](=[O:25])/[CH:20]=[CH:21]/[CH:22]1[CH2:24][CH2:23]1.C(O)(C(F)(F)F)=O.C1CCCCC1>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH3:17][O:18][C:19]([CH:20]1[CH:21]([CH:22]2[CH2:24][CH2:23]2)[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12]1)=[O:25]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 8078CyclohexaneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 145855512-Propenoic acid, 3-cyclopropyl-, methyl ester

生成物 1

HCID 68647670Methyl 1-benzyl-4-cyclopropylpyrrolidine-3-carboxylate収率 32.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒4 回HCID 21867204Cyclohexane ethylacetate溶媒

実験手順

101.1 To a stirred, cooled (0° C.) solution of 3.18 g N-benzyl-N-(methoxymethyl)trimethyl-silylmethylamine (CAS 93102-05-7) in 30 ml CH2Cl2 under an argon atmosphere was added dropwise a solution of 1.69 g (E)-3-cyclopropyl-acrylic acid methyl ester (CAS 59939-11-6; J. Org. Chem. 1990, 55(10), 3097) in 15 ml CH2Cl2 over a period of 20 min. Then a solution of 0.1 ml TFA in 5 ml CH2Cl2 was added dropwise within 10 min. When addition was complete, the mixture (slowly warming up to room temperature) was stirred overnight. Then, the mixture was diluted with CH2Cl2, washed with sat. aq. NaHCO3 and brine, dried over MgSO4, filtered and concentrated. The crude product was isolated by chromatography (silica gel; (gradient: cyclohexane->cyclohexane/EtOAc 7:3) to give 1.14 g (3RS,4RS)-1-benzyl-4-cyclopropyl-pyrrolidine-3-carboxylic acid methyl ester as light yellow oil. MS 260.3 ([M+H]+)

後処理

  1. additionWhen addition
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was isolated by chromatography (silica gel

出典と根拠

ORDレコード
ord-d510df7ec5e74d2c98518136a1e9ba86
出典データセット
uspto-grants-2010_10
特許番号
US07820699B2

反応ノート

読み込み中…