1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69995593, compound

HRID 1359861Notes

Reaction equation

HRID 1359861 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH:17]1([NH:20][CH3:21])[CH2:19][CH2:18]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=[O:15])[N:20]([CH:17]1[CH2:19][CH2:18]1)[CH3:21])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 18546974N-methylcyclopropanamine hydrochloride

Product 1

HCID 69995593HCID 69995593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (788 mg, 1 eq.), cyclopropyl-methyl-amine hydrochloride (478 mg, 1.2 eq.), HOBt (7.48 mg, 1.5 eq.), EDAC (1.05 g, 1.5 eq.) and TEA (1.5 mL, 3 eq.) in DMF (15 mL) was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate and extracted with DCM. The combined DCM was washed with brine, dried, concentrated, purified on a silica gel column to give (R)-2-(cyclopropyl-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with sodium bicarbonate
  3. extractionextracted with DCM
  4. washThe combined DCM was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified on a silica gel column

Sources & evidence

ORD record
ord-974934178b8841bdb7a16891538ccaae
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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