Sodium hydride → 3-(3-Bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one

HRID 2037415Notes

Reaction equation

HRID 2037415 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6](=[O:8])[NH:5][CH2:4][CH2:3]1.[H-].[Na+].[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br>C1COCC1>[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][N:5]1[CH2:4][CH2:3][C:2]([CH3:1])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6]1=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 534742826-Methyl-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 251824193-(3-Bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-oneYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-methyl-6-phenyl-1,3-oxazinan-2-one (500 mg, 2.62 mmol) and NaH (189 mg, 7.86 mmol) in dry THF (10 mL) was stirred for 1 h. A solution of m-bromobenzyl bromide (1.31 g, 5.24 mmol) in dry THF (3 mL) was added. The mixture was stirred overnight at rt. The reaction mixture was quenched water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by preparative TLC to afford 3-(3-bromobenzyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (300 mg, 32%). 1H NMR (CDCl3): 1.60-1.70 (s, 3H), 2.15-2.30 (m, 1H), 2.35-2.48 (m, 1H), 2.79-2.90 (m, 1H), 3.00-3.10 (m, 1H), 4.30-4.40 (m, 1H), 4.50-4.60 (m, 1H), 6.90-7.00 (m, 1H), 7.00-7.10 (m, 1H), 7.20-7.45 (m, 7H).

Workup

  1. customThe reaction mixture was quenched water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by preparative TLC

Sources & evidence

ORD record
ord-c4c12095ae4d47a99d1836af690e964f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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