1,2-Dichloroethane → (2R,4R)-2-cyclopropylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1839838Notes

Reaction equation

HRID 1839838 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([O:9][C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@@H:13]1[C:18](O)=[O:19])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@@H:13]1[C:18](=[O:19])[NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 688616N-Boc-cis-4-hydroxy-D-proline

Product 1

HCID 69741572(2R,4R)-2-cyclopropylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropylamine was coupled with (2R,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (8 g), EDC, HOBt, TEA in DMF to give 5 g of (2R,4R)-2-cyclopropylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester as a white semi-solid.

Sources & evidence

ORD record
ord-810a87fcf83a41008c003f4eb5248d9d
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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