2-Bromoethanol → HCID 45087381, compound

HRID 1522854Notes

Reaction equation

HRID 1522854 reaction equation
Cl.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:9][CH2:10][OH:11].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][OH:11]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 11147704(2R)-(-)-2-Methylpyrrolidine hydrochloride

Product 1

HCID 45087381HCID 45087381, compoundYield 24,020.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-2-methylpyrrolidine hydrochloride (4 g, 0.03 mol), 2-bromoethanol (3.7 g, 0.029 mmol) and K2CO3 (8.28 g, 0.0618 mol) in acetonitrile (50 mL) was stirred at room temperature overnight. The mixture was filtered, and the filter cake was washed with ethyl acetate (100 mL). The combined filtrate was concentrated and the residue was purified on a silica gel column (MeOH/DCM=1/50) to give (R)-2-(2-methylpyrrolidin-1-yl)ethanol (0.9 g) as a colorless oil. 1H NMR (CDCl3): δ 3.63 (m, 2H), 3.14 (m, 1H), 2.95 (m, 1H), 2.44 (m, 1H), 2.24 (dt, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 2H), 1.38 (m, 1H), 1.07 (d, 3H); LCMS: 130 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethyl acetate (100 mL)
  3. concentrationThe combined filtrate was concentrated
  4. customthe residue was purified on a silica gel column (MeOH/DCM=1/50)

Sources & evidence

ORD record
ord-ef3f4a0e23b040a5b343cdbe79b2daa7
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

Loading…