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

HRID 722394

Reaction equation

HRID 722394 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-cf93205eec9a4ce9903197ec4224011e
Source dataset
uspto-grants-2006_11
Patent number
US07138423B2

Linked notes

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