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

HRID 722394

反応式

HRID 722394 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-cf93205eec9a4ce9903197ec4224011e
出典データセット
uspto-grants-2006_11
特許番号
US07138423B2

関連ノート

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