Diisopropylamine → rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 527470Notes

Reaction equation

HRID 527470 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][N:10](CC2C=CC=CC=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(NC(C)C)(C)C.C(OC(Cl)C)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 153309271-ChloroethylformateHCID 67237396rac-(3S,4R)-[1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 67237824rac-(3S,4R)-[4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl esterYield 153%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of rac-(3S,4R)-[1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (5.59 g, 0.013 mol) and N,N-diisopropylamine (6.81 mL, 0.017 mol) in toluene (60 mL) was added at ambient temperature 1-chloroethyl formate (1.88 mL, 0.017 mol) and the reaction mixture was stirred for 24 h. It was concentrated and the resulting residue was diluted in methanol (60 mL) and stirred for 3 h at ambient temperature. Concentration afforded the crude title compound (6.59 g, 67% purity) as a light brown solid which was directly used without further purification.

Workup

  1. concentrationIt was concentrated
  2. additionthe resulting residue was diluted in methanol (60 mL)
  3. stirringstirred for 3 h at ambient temperature
  4. concentrationConcentration

Sources & evidence

ORD record
ord-adee08ad31424aa8aae613e34fc3fc3c
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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