1-Cyano-2-(1-ethyl-propyl)-cyclopropanecarboxylic acid benzyl ester → 1-Aminomethyl-2-(1-ethyl-propyl)-cyclopropanecarboxylic acid

HRID 1796832ノート

反応式

HRID 1796832 の反応式
C([O:8][C:9]([C:11]1([C:19]#[N:20])[CH2:13][CH:12]1[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:10])C1C=CC=CC=1>C1COCC1.[Pd]>[NH2:20][CH2:19][C:11]1([C:9]([OH:10])=[O:8])[CH2:13][CH:12]1[CH:14]([CH2:15][CH3:16])[CH2:17][CH3:18]

参加物

4

反応物 1

HCID 453578991-Cyano-2-(1-ethyl-propyl)-cyclopropanecarboxylic acid benzyl ester

生成物 1

HCID 103751581-Aminomethyl-2-(1-ethyl-propyl)-cyclopropanecarboxylic acid収率 11%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-cyano-2-(1-ethyl-propyl)-cyclopropanecarboxylic acid benzyl ester (1.76 g, 6.5 mmol) in 25 mL THF was added 20% Pd/C (0.2 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 3 hours. 1H NMR analysis indicated the benzyl ester had been completely cleaved. The mixture was filtered and concentrated hydrochloric acid (2 g) was added along with PtO2 (0.42 g) and the mixture was hydrogenated for an additional 16 hours until the nitrile was reduced. The mixture was filtered and concentrated. Flash chromatography of the residue on silica gel (0.25:1.25:3.5 conc. NH4OH (aq):MeOH:CH2Cl2), followed by ion-exchange chromatography on a DOWEX-50WX8-100 resin provided 0.13 g (11%) of 1-aminomethyl-2-(1-ethyl-propyl)-cyclopropanecarboxylic acid as a colorless solid, mp 255–257° C.: 1H NMR (D2O) δ 3.53 (d, J=13.2 Hz, 1H), 2.50 (d, J=13.2 Hz, 1H), 1.30 (m, 3H), 1.08–1.23 (m, 4H), 0.74 (t, J=7.6 Hz, 3H), 0.65 (t, J=7.6 Hz, 3H), 0.54 (m, 1H). LRMS: m/z 184.1 (M−1). Anal. Calcd for C10H19NO2: C, 64.83; H, 10.34; N, 7.56. Found: C, 64.84; H, 10.69; N, 7.44.

後処理

  1. filtrationThe mixture was filtered
  2. additionconcentrated hydrochloric acid (2 g) was added along with PtO2 (0.42 g)
  3. waitthe mixture was hydrogenated for an additional 16 hours until the nitrile
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b860c998fb854674b7f0f05971f0538e
出典データセット
uspto-grants-2006_04
特許番号
US07030267B2

反応ノート

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