HCID 18672287, compound → 3-Phenylpyrrolidine-2-carboxylic acid

HRID 1058325Notes

Reaction equation

HRID 1058325 reaction equation
C([O:3][C:4]([C:6]1(C(OCC)=O)[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][NH:7]1)=[O:5])C.CC1(C)CCNC1C(O)=O.C(C1(C(OCC)=O)C(C)(C)CCN1)(OCC)=O>>[C:11]1([CH:10]2[CH2:9][CH2:8][NH:7][CH:6]2[C:4]([OH:5])=[O:3])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 18672287HCID 18672287, compoundHCID 21864153HCID 21864153, compoundHCID 21866189Diethyl 3,3-dimethylpyrrolidine-2,2-dicarboxylate

Product 1

HCID 38972813-Phenylpyrrolidine-2-carboxylic acid

Procedure

3-Phenyl-D,L-proline was prepared from diethyl-3-phenylpyrrolidine-2,2-dicarboxylate (2.82 g, 9.70 mmol) essentially according to the procedure described in U.S. Pat. No. 4,060,603 for the preparation of 3,3-dimethyl-D,L-proline from 2,2-dicarboethoxy-3,3-dimethylpyrrolidine. The product was isolated as a brown oil. LCMS RT=0.62 min. LCMS (M+H)=191.9. 1H NMR (CD3OD, 400 MHz): δ 7.36-7.28 (m, 5H), 4.60 (d, J=9.2 Hz, 1H), 3.97 (apparent q, J=8.4 Hz, 1H), 3.77-3.71 (m, 1H), 3.48-3.41 (m, 1H), 2.58-2.50 (m, 1H), 2.43-2.33 (m, 1H).

Workup

  1. customThe product was isolated as a brown oil

Sources & evidence

ORD record
ord-9c151671b5994addbafba60d97f2f47f
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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