Methyl chloroformate → Methyl 3-(4-bromophenyl)pyrrolidine-1-carboxylate

HRID 1054600Notes

Reaction equation

HRID 1054600 reaction equation
C(N(CC)CC)C.Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:12][CH:11]=1.Cl[C:22]([O:24][CH3:25])=[O:23]>C1COCC1.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:20][CH2:19][N:18]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 534077083-(4-Bromophenyl)pyrrolidine hydrochloride

Product 1

HCID 84210133Methyl 3-(4-bromophenyl)pyrrolidine-1-carboxylateYield 111.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (192 mg, 1.9 mmol) was added to a suspension of 3-(4-bromophenyl)pyrrolidine hydrochloride (200 mg, 0.76 mmol) in anhydrous THF (5 mL). The reaction mixture was stirred for 5 minutes and treated with methyl chloroformate (0.1 g, 1.05 mmol). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with water and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give methyl 3-(4-bromophenyl)pyrrolidine-1-carboxylate (0.24 g, quantitative yield) as an oil which was used for next step directly. MS (ES+) 283.9 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours at room temperature
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-284611099a764e4fa4c2cf7407cf27a0
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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