Methyl morpholine oxide → HCID 86606879, compound

HRID 749423Notes

Reaction equation

HRID 749423 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:19][CH:20]=C)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:26]CC1.S(=O)(O)[O-].[Na+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.C(O)(C)(C)C.O.C1COCC1.[Cl-].[Na+].O.O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:19][CH:20]=[O:26])[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

11

Reactant 4

HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 23667635Sodium periodateHCID 86606880HCID 86606880, compound

Product 1

HCID 86606879HCID 86606879, compoundYield 87.7%

Reagents, catalysts & solvents 6

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent4×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl [(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]methylcarbamate (1.8 g, 6.1 mmol) was dissolved in a mixture of acetone (32 mL), tert-butanol (16 mL) and water (8 mL). The solution was stirred at room temperature during addition of OsO4 (0.64 mL of 2.5% in tert-butanol, 0.06 mmol) and 4-methylmorpholine N-oxide (3.2 g, 27 mmol). The mixture was stirred at room temperature for 4 h. A saturated aqueous solution of sodium bisulfite (60 mL) was added and the mixture stirred for 20 min and then diluted with water (100 mL). The solution was extracted twice with CH2Cl2 and the combined organic solutions were washed with brine. The solvent removed by evaporation and the residue (2.4 g) was dissolved in a mixture of THF (28 mL) and water (12 mL) whereupon sodium periodate (1.44 g, 6.7 mmol) was added. The solution was stirred at room temperature for 4.5 h and then diluted with water and brine. The mixture was extracted twice with CH2Cl2 and the combined organic solutions were dried over MgSO4. The solvent was removed by evaporation and there was obtained 1.58 g (87%) of tert-butyl [(2S)-2-(4-fluorophenyl)-4-oxobutyl]methylcarbamate. 1H NMR (500 MHz, CDCl3): 1.4 (s, 9H), 2.6-2.8 (m, 5H), 3.2-3.6 (cm, 3H), 7.0 (m, 2H), 7.1 (b, 2H), 9.7 (s, 1H).

Workup

  1. stirringthe mixture stirred for 20 min
  2. extractionThe solution was extracted twice with CH2Cl2
  3. washthe combined organic solutions were washed with brine
  4. customThe solvent removed by evaporation
  5. additionwas added
  6. stirringThe solution was stirred at room temperature for 4.5 h
  7. extractionThe mixture was extracted twice with CH2Cl2
  8. dry with materialthe combined organic solutions were dried over MgSO4
  9. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-a52ea4d0acac47edb6efb3cc45032330
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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