Sodium hydride → HCID 57650070, compound

HRID 2063494Notes

Reaction equation

HRID 2063494 reaction equation
[O:1]=[C:2]([CH3:21])[CH2:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:5].[H-].[Na+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>C1COCC1>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][CH:3]([C:2](=[O:1])[CH3:21])[C:4]([C@H:6]2[CH2:10][CH2:9][CH2:8][N:7]2[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:5])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 57650043HCID 57650043, compound

Product 1

HCID 57650070HCID 57650070, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (R)-benzyl 2-(3-oxobutanoyl)pyrrolidine-1-carboxylate (1 g, 3.5 mmol) in THF (50 mL) was added sodium hydride (130 mg, 5.3 mmol) followed by 4-chlorobenzyl bromide (710 mg, 3.5 mmol). The reaction mixture was then heated at 60° C. for 6 h. After concentrating the reaction mixture in vacuo, the resulting residue was purified by silica gel column chromatography (hexanes ethyl acetate) to afford (2R)-benzyl 2-(2-(4-chlorobenzyl)-3-oxobutanoyl)pyrrolidine-1-carboxylate (300 mg, 21%). LCMS: 8.04 and 8.14 min, calculated: 413, found (MH+): 414.

Workup

  1. concentrationAfter concentrating the reaction mixture in vacuo
  2. customthe resulting residue was purified by silica gel column chromatography (hexanes ethyl acetate)

Sources & evidence

ORD record
ord-179c4545a89f4295847853a76b6e2940
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…