1,4-Dibromobutane → 2-Methyl-2-(pyrrolidin-1-yl)propan-1-ol

HRID 1387104Notes

Reaction equation

HRID 1387104 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].Br[CH2:8][CH2:9][CH2:10][CH2:11]Br.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:5][C:2]([N:1]1[CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:6])[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 223118122-Methyl-2-(pyrrolidin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-2-methyl-1-propanol (15 g, 168.3 mmol), 1,4-dibromobutane (18.2 g, 84.1 mmol), and K2CO3 (48.8 g, 353.4 mmol) in 1 L of THF was heated at 60° C. for 4.5 days. After cooling to ambient temperature, the reaction mixture was filtered and concentrated in vacuo. Flash chromatography (SiO2; 94:4:2 EtOAc/MeOH/TEA) afforded 8.21 g (57.3 mmol; 34%) of the title product as a pale yellow oil. A small sample was dissolved in EtOAc and treated with one equivalent of oxalic acid in a method similar to Example 1, Part C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99bb64531a2e4ef5a592719bc9d1031f
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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