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

HRID 2037415노트

반응식

HRID 2037415 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4c12095ae4d47a99d1836af690e964f
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575156B2

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