benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride → HCID 178525081, compound

HRID 1385748Notes

Reaction equation

HRID 1385748 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C@H:17]1([C:26]([OH:28])=O)[CH2:22][CH2:21][C@@H:20]([C:23]([OH:25])=O)[CH2:19][CH2:18]1>CCOC(C)=O>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:26]([C@H:17]1[CH2:18][CH2:19][C@@H:20]([C:23]([N:12]2[CH2:13][CH2:14][CH2:15][C@@H:11]2[C:10]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:16])=[O:25])[CH2:21][CH2:22]1)=[O:28])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochlorideHCID 178418675HCID 178418675, compound

Product 1

HCID 178525081HCID 178525081, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using General Procedure A with 2.0 g (8.2 mmol) D-Proline benzyl ester hydrochloride and 700 mg (4.1 mmol) cis-cyclohexane-1,4-dicarboxylic acid afforded, after flash chromatography (EtOAc), 2.0 g (91%) of the title compound as a colorless oil. MS m/e (%): 547 (M+H+, 100).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-e33eb2ff42f148c9a908d1c4a1f16016
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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