Hydrochloric Acid → trans-Ethyl-4-phenylpyrrolidine-3-carboxylate hydrochloride

HRID 722394

반응식

HRID 722394 반응식
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2].[ClH:24]>[Pd].C(O)C>[ClH:24].[CH2:1]([O:3][C:4]([C@H:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 12922288trans-Ethyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate

생성물 1

HCID 131726062trans-Ethyl-4-phenylpyrrolidine-3-carboxylate hydrochloride

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of trans-ethyl-1-benzyl-4-phenylpyrrolidine-3-carboxylate (1.69 g, 5.47 mmol), concentrated HCl (36% in H2O, 610 mg) and palladium on activated carbon (10 wt %, 169 mg) in ethyl alcohol (27 mL) was put on hydrogenator at 50 psi for overnight. The mixture was filtered through Celite pad and washed with ethyl alcohol. The filtrated was concentrated to give the title compound as a off-white solid (quantitative yield). 1H NMR (400 MHz, CD3OD) δ 1.11 (3H, t, J=6.8 Hz), 3.36–3.42 (2H, m), 3.63–3.75 (4H, m), 4.06–4.11 (2H, m), 7.29–7.39 (5H, m). HPLC purity (retention time): 95% (1.05 min, method C). MS: 220.23 (MH+).

후처리

  1. filtrationThe mixture was filtered through Celite pad
  2. washwashed with ethyl alcohol
  3. concentrationThe filtrated was concentrated

출처 및 근거

ORD 기록
ord-cf93205eec9a4ce9903197ec4224011e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138423B2

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