1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

HRID 1359740Notes

Reaction equation

HRID 1359740 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=N[CH2:24][CH2:25][CH2:26][N:27]([CH3:29])C.C1C=CC2N(O)N=NC=2C=1.N1CCCC1>CN(C=O)C.O.C(=O)(O)[O-].[Na+]>[CH2:4]([O:3][C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13]([N:27]1[CH2:26][CH2:25][CH2:24][CH2:29]1)=[O:15])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate

Product 1

HCID 667614(R)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of (+)-carbobenzyloxy-D-proline (1.5 g, 6 mmol), EDAC (2.3 g, 12 mmol), HOBt (800 mg, 6 mmol), TEA (1.5 mL) and pyrrolidine (853 mg, 12 mmol) in DMF (20 mL) was stirred at rt for 18 hours. The reaction was diluted with water and sodium bicarbonate, extracted with DCM (3×). The combined DCM was concentrated and purified on a silica gel column to give (R)-2-(pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester.

Workup

  1. extractionextracted with DCM (3×)
  2. concentrationThe combined DCM was concentrated
  3. custompurified on a silica gel column

Sources & evidence

ORD record
ord-5f9f8fbc16794791adcba827f64da92a
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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