Sodium hydride → HCID 57650070, compound

HRID 2063484Notes

Reaction equation

HRID 2063484 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 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-benzyl 2-(3-oxobutanoyl)pyrrolidine-1-caboxylate (670 mg, 2.32 mmol) in anhydrous THF (20 mL) was added sodium hydride (111 mg, 60 wt. % in mineral oil, 2.78 mmol). The mixture was stirred at room temperature for 30 min and added to a solution of 4-chlorobenzyl bromide (715 mg, 3.48 mmol) in THF (10 mL). The reaction mixture was stirred at 60° C. for 18 h and then the solvents were removed in vacuo. Purification of the resulting residue by silica gel column chromatography (ethyl acetate/hexane gradient, 10-100% EtOAc) afforded the desired product (812 mg, 86%). MS: calculated: 413.14, found (MH+): 414.3.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 18 h
  2. customthe solvents were removed in vacuo
  3. customPurification of the resulting residue by silica gel column chromatography (ethyl acetate/hexane gradient, 10-100% EtOAc)

Sources & evidence

ORD record
ord-cb27978c9a5c4f8b86c378a9e46f3870
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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