Methyl morpholine oxide → 3-cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

HRID 749451노트

반응식

HRID 749451 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][CH:20]=C)[CH3:16])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].C[N+]1([O-])CC[O:33]CC1.OS([O-])=O.[Na+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.C(O)(C)(C)C.O.[Cl-].[Na+].O.O=[Os](=O)(=O)=O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([N:15]([CH2:17][C@H:18]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][CH:20]=[O:33])[CH3:16])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

참가 물질

10

반응물 4

HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 23667635Sodium periodateHCID 689785133-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

생성물 1

HCID 113264143-cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide수율 89.9%

시약·촉매·용매 5

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매3회HCID 6386tert-Butanol용매HCID 57417360Sodium chloride; water용매

실험 절차

3-Cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide (460 mg, 1.22 mmol) was dissolved in a mixture of acetone (8 mL), t-butyl alcohol (4 mL) and water (2 mL) under nitrogen. OsO4 (2.5% in t-butyl alcohol, 0.165 mL, 0.01 mmol) was added together with 4-methylmorpholine-4-oxide (630 mg, 5.4 mmol). The solution was stirred at room temperature for 5 h and then an aqueous solution of NaHSO3 (39%, 12 mL) was added. The mixture was stirred for 15 min, diluted with water (50 mL) and then extracted three times with CH2Cl2. The organic solution was dried over Na2SO4 and then the solvent was evaporated. The residue (570 mg) is was dissolved in a mixture of THF (7 mL) and water (3 mL) and to the resultant solution was added sodium periodate (287 mg, 1.34 mmol). The mixture was stirred at room temperature overnight, diluted with water (50 mL) and brine (30 mL) and then extracted twice with CH2Cl2. The organic solution was dried over Na2SO4 and then the solvent was evaporated. There was obtained 415 mg (89%) of 3-cyano-N-[(2S)-2-(4-fluorophenyl)-4-oxobutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide as an oil. 1H NMR (400 MHz, CDCl3): 1.4-4.2 (cm, 16H), 6.6-7.4 (cm, 6H), 9.7 (s, 1H); LCMS: m/z 379 (M+1)+.

후처리

  1. stirringThe mixture was stirred for 15 min
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customthe solvent was evaporated
  5. dissolutionThe residue (570 mg) is was dissolved in a mixture of THF (7 mL) and water (3 mL) and to the resultant solution
  6. stirringThe mixture was stirred at room temperature overnight
  7. extractionextracted twice with CH2Cl2
  8. dry with materialThe organic solution was dried over Na2SO4
  9. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-3a206ef5c9904d9d8aeb47a1886a68be
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

반응 노트

불러오는 중…