Tert-butyl 3-oxopyrrolidine-1-carboxylate → Tert-butyl 3-(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)pyrrolidine-1-carboxylate

HRID 2371162Notes

Reaction equation

HRID 2371162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:18]([N:25]1[CH2:29][CH2:28][C:27](=O)[CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH:28]3[CH2:27][CH2:26][N:25]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:29]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 16775732N-(3,4-Dichlorophenyl)piperazine-1-carboxamide

Product 1

HCID 57656740Tert-butyl 3-(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)pyrrolidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,4-dichlorophenyl)piperazine-1-carboxamide (0.548 g, 2 mmols) and 1-N-BOC-3-pyrrolidinone (370 mg, 2 mmols) were stirred at room temperature in dichloromethane (20 ml) for approximately 15 minutes. Added to this mixture was sodium triacetoxyborohydride (1.06 g, 5 mmols) and the reaction stirred overnight at room temperature. Saturated sodium bicarbonate solution (5 ml) was added and the mixture stirred for 1 hour then poured onto a hydromatrix column and the product eluted with dichloromethane (100 ml). The crude product was subjected to chromatography on silica gel (50 g) using a gradient of 100% dichloromethane through to 10% methanolic ammonia in dichloromethane to give the title compound as a white solid (780 mg).

Workup

  1. additionAdded to this mixture
  2. stirringthe mixture stirred for 1 hour
  3. additionthen poured onto a hydromatrix column
  4. washthe product eluted with dichloromethane (100 ml)

Sources & evidence

ORD record
ord-b6664c3020db4a2e8ff25157af194f1e
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

Loading…