1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69998257, compound

HRID 1359834Notes

Reaction equation

HRID 1359834 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 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 18546974N-methylcyclopropanamine hydrochloride

Product 1

HCID 69998257HCID 69998257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1 eq.), cyclopropyl-methyl-amine hydrochloride (1.2 eq.), HOBt (1.5 eq.), EDAC (1.5 eq.) and TEA (3 eq.) in DMF 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 (S)-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-6189b16fdc344efba8606853a6e69b7f
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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