3-Bromo-1-propanol → 3-[(2R)-2-Methylpyrrolidin-1-yl]propan-1-ol

HRID 272930Notes

Reaction equation

HRID 272930 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[CH3:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1.[OH-].[K+]>O>[NH3:8].[CH3:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:2][CH2:3][CH2:4][OH:5]

Participants

6

Reactant 3

HCID 123083-Bromo-1-propanolHCID 14797Potassium HydroxideHCID 641544(R)-2-Methylpyrrolidine

Product 2

HCID 222AmmoniaHCID 574575603-[(2R)-2-Methylpyrrolidin-1-yl]propan-1-olYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Bromopropan-1-ol (5.28 mL, 58.4 mmol) was added to a solution of (R)-2-methylpyrrolidine (7.1 g, 58.4 mmol) in water (200 mL). KOH (7.53 g, 134 mmol) was then added and the mixture stirred at ambient temperature for 48 hours. The reaction mixture was then extracted with dichloromethane (5×80 mL) and ethyl acetate (5×80 mL). The combined organic extracts were dried using MgSO4, filtered and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, (90:10:1) to give the title compound as a pale brown oil (5.44, 65%). LCMS (APCI+) 144 (M+H)+.

Workup

  1. extractionThe reaction mixture was then extracted with dichloromethane (5×80 mL) and ethyl acetate (5×80 mL)
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe compound was purified by column chromatography on Biotage® silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7c1f6287be084aeea3f72847f4bb79fc
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

Loading…