Benzyl Bromide → HCID 11106861, compound

HRID 887392Notes

Reaction equation

HRID 887392 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:8](Br)[C:9]1C=C[CH:12]=[CH:11][CH:10]=1.C[CH2:17][O:18][C:19](C)=[O:20]>C(Cl)Cl>[CH2:1]([N:3]1[CH2:6][CH2:7][CH2:5][C@H:4]1[C:19]([O:18][CH3:17])=[O:20])[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 11106861HCID 11106861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-proline methyl ester hydrochloride (5.8 g, 35 mmol) was suspended in DCM (40 mL), to it was added triethylamine (12 ml, 84 mmol). After stirring for 10 min, the precipitate formed was filtered off and washed with DCM (5 mL). To the filtrate was added benzyl bromide (5.0 ml, 42 mmol). The reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with EtOAc and washed with water and brine, dried (Na2SO4) and concentrated. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 25% EtOAc in hexane, to provide (S)-methyl 1-benzylpyrrolidine-2-carboxylate as colorless oil. MS (ESI, pos. ion) m/z: 220.0 (M+1).

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with DCM (5 mL)
  4. stirringThe reaction mixture was stirred at RT for 16 h
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g)
  9. washeluting with a gradient of 0% to 25% EtOAc in hexane

Sources & evidence

ORD record
ord-18c4a82b3521473393785fec34bd7fd5
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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