Pyrrolidine → (1R)-1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethanol

HRID 2114446Notes

Reaction equation

HRID 2114446 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:9])[CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 11217859(R)-4-Bromostyrene oxideHCID 71586775Bentonite

Product 1

HCID 28350021(1R)-1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethanolYield 43.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-(4-Bromophenyl)oxirane (49.93 g, 250.8 mmol) was added to pyrrolidine (35 mL, 421.2 mmol) in a CH2Cl2 (150 mL) solution at 0° C. with magnetic stirring. Montmorillonite K10 clay (5.87 g) was added in one portion. The resulting mixture was stirred at room temperature for 16 h. The mixture was then filtered through a pad of Celite and the filtrate was concentrated to give a white solid. The crude material was recrystallized from Et2O to give (1R)-1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethanol as clear crystals (29.43 g, 109 mmol, 43% yield). MS (ES) m/e 272, 270 [M+H]+

Workup

  1. filtrationThe mixture was then filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customto give a white solid
  4. customThe crude material was recrystallized from Et2O

Sources & evidence

ORD record
ord-0e6c8bf1f57d4107b3559b9e0372fef6
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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