Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2-Methyl-2-pyrrolidin-1-yl-propionic acid ethyl ester

HRID 1181350Notes

Reaction equation

HRID 1181350 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>>[CH3:8][C:2]([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 2

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 31268Pyrrolidine

Product 1

HCID 140443752-Methyl-2-pyrrolidin-1-yl-propionic acid ethyl esterYield 74%

Conditions

Temperature
70 °C

Procedure

Ethyl 2-bromo-2-methylpropanoate (0.6800 g, 3.4861 mmol) was taken up in pyrrolidine (4 mL) and heated to 70° C. The reaction was stirred for 18 h and then concentrated. The residue was taken up in EtOAc (100 mL) and washed with water (1×100 mL), dried over MgSO4, filtered and concentrated to afford 0.4754 g (2.5697 mmol, 74%) of the product. 1H NMR (CDCl3) δ 4.16 (q, 2H, J=7.1 Hz), 2.76 (bs, 4H), 1.76 (bs, 4H), 1.36 (s, 6H), 1.27 (t, 2H, J=7.1 Hz).

Workup

  1. concentrationconcentrated
  2. washwashed with water (1×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b23f3f246ae4adc84f03f1781c40eff
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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