HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → 3-[(4-Chloro-benzyl)-methoxycarbonylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 242625
Notes
Print preview

Reaction equation

HRID 242625 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N+]([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][O:26][C:27](=[O:30])[CH2:28]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:28][C:27]([O:26][CH3:25])=[O:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 66758130HCID 66758130, compound

Product 1

HCID 667583843-[(4-Chloro-benzyl)-methoxycarbonylmethyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-Chloro-2-nitro-benzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.8 g, 10.7 mmol) in DMF (40 mL) was added Bromo-acetic acid methyl ester (1.01 mL, 10.7 mmol) and K2CO3 (1.48 g, 10.7 mmol). The resultant suspension was stirred at 70° C. overnight. The reaction mixture was diluted with water and ethyl ether. The organic extract was dried over MgSO4, filtered and concentrated to provide the desired product as an oil. The crude product was purified on SiO2 and concentrated to provide the desired product as an oil (2 g, 44%). LCMS (retention time=3.03, ES+428)

Workup

  1. extractionThe organic extract
  2. dry with materialwas dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-66d6968f0c484200ae540f79816670c9
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653096B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes