Triethylamine → HCID 69994491, compound

HRID 1359702Notes

Reaction equation

HRID 1359702 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH:44]1[CH2:48][CH2:47][C@@H:46]([OH:49])[CH2:45]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([N:44]1[CH2:48][CH2:47][C@@H:46]([OH:49])[CH2:45]1)=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 69994491HCID 69994491, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(tert-butoxycarbonyl)-L-proline (2 g, 9.3 mmol), EDAC (3.5 g, 18 mmol), HOBt (1.35 g, 10 mmol) in DMF (20 mL) was added triethylamine (2 mL, 14 mmol) and (R)-(+)-3-pyrrolidinol (1.5 mL, 18 mmol). After stirring at room temperature for 48 h, the reaction was quenched with water and sodium bicarbonate solution. It was then extracted with 5% of methanol in dichloromethane. The residue was purified on a silica gel column eluting with 10% of methanol in dichloromethane to give 2.2 g (83%) of (S)-2-((R)-3-hydroxy-pyrrolidin-1-ylcarbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customthe reaction was quenched with water and sodium bicarbonate solution
  2. extractionIt was then extracted with 5% of methanol in dichloromethane
  3. customThe residue was purified on a silica gel column
  4. washeluting with 10% of methanol in dichloromethane

Sources & evidence

ORD record
ord-c3cb4050702e450a9bda3c0beb52be9d
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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