2-Pyrrolidone → HCID 21923262, compound

HRID 1920746Notes

Reaction equation

HRID 1920746 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].Br[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C1COCC1>[C:14]([O:13][C:11](=[O:12])[CH2:10][N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 21923262HCID 21923262, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-pyrrolidone (2.66 ml, 34 mmol) and NaH (60% in oil, 1.25 g, 31.3 mmol) in THF (75 ml) was stirred until gas evolution ceased (30 min). tert-Butyl 2-bromoacetate (4.45 ml, 30 mmol) was added and stirred at r.t. overnight then partitioned between water (200 ml) and ethyl acetate (200 ml) to give intermediate 2-(oxo-pyrrolidin-1-yl)-acetic acid tert-butyl ester (5.8 g). It was dissolved in acetic acid (40 ml) and conc. aq. HCl (6 ml) with gas evolution observed. After stirring at r.t. for 2 hours it was evaporated and recrystallized from toluene/ethanol to give 2.58 g of the title compound (60% yield). 1H NMR (500 MHz, DMSO-d6): 1.95 (quintet, J=7.7 Hz, 2H), 2.24 (t, J=8.1 Hz, 2H), 3.38 (m, overalapping with H2O (3.35 ppm), 2H), 3.91 (s, 2H), 12.77 (br., 1H).

Workup

  1. custom(30 min)
  2. stirringstirred at r.t. overnight
  3. customthen partitioned between water (200 ml) and ethyl acetate (200 ml)

Sources & evidence

ORD record
ord-316449c454d34c98ab8938438a6bef93
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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