1,2-Dichloroethane → HCID 66936246, compound

HRID 1366441Notes

Reaction equation

HRID 1366441 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]([C@H:5]1[C@H:9]([CH3:10])[CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[CH2:6]1)=[O:4].C(Cl)CCl.CNC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][N:2]([CH3:21])[C:3]([C@H:5]1[C@H:9]([CH3:10])[CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 131728710HCID 131728710, compound

Product 1

HCID 66936246HCID 66936246, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of commercially available phenylmethyl (trans)-3-[(dimethylamino)carbonyl]-4-methyl-1-pyrrolidinecarboxylate (1.06 g, 3.4 mmol), DMAP (0.63 g, 5.2 mmol), and EDC (1.0 g, 5.2 mmol) in DCM (18 mL) was stirred for 5 min and dimethylamine (1.9 mL, 3.8 mmol, 2M in THF) was added. The reaction was allowed to stir until it was judged to be complete by LCMS and was quenched with 1 M HCl. A standard work-up provided the desired amide intermediate. This material was immediately dissolved in degassed MeOH (20 mL) and 10% Pd/C (120 mg) was added. The reaction mixture was allowed to stir under a hydrogen balloon until complete deprotection was observed by LCMS. The catalyst was removed by filtration to yield (trans)-N,N,4-trimethyl-3-pyrrolidinecarboxamide. LCMS: (M+H)+: 157.2.

Workup

  1. customwas quenched with 1 M HCl

Sources & evidence

ORD record
ord-2968d9b774e2413e8c9ea80e18cc88df
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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