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

HRID 1796832노트

반응식

HRID 1796832 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b860c998fb854674b7f0f05971f0538e
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030267B2

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