tert-Butanol → HCID 9840562, compound

HRID 1066725Notes

Reaction equation

HRID 1066725 reaction equation
[CH:1]12CC(C=[CH:6]1)[CH2:3][CH:2]2[O:8][C:9]1[CH:18]=[N:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[N:10]=1.C[N+]1([O-])CC[O:27]CC1.[C:31]([OH:35])([CH3:34])([CH3:33])C>C1COCC1.O=[Os](=O)(=O)=O>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:21][CH3:22])[N:10]=[C:9]([O:8][CH:2]1[CH2:3][CH:34]3[CH2:6][CH:1]1[CH:33]([OH:27])[CH:31]3[OH:35])[CH:18]=[N:17]2

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 22573128HCID 22573128, compound

Product 1

HCID 9840562HCID 9840562, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(bicyclo[2.2.1]hept-5-en-2-yloxy)-6,7-dimethoxy-quinoxaline (149 mg, 0.5 mmole) and 4-methylmorpholine N-oxide (234 mg, 2 mmole) at room temperature in 5 mL of THF is added a solution of OsO4 in t-butanol (2.5% by wt., 0.2 mL). The brown solution is stirred vigorously for two hours before being quenched with saturated NaHS2O3 (2 mL). Ether (3×100 mL) is used to extract and then dried over magnesium sulfate. The residue after filtration and concentration is chromatographed on silica ;gel (50% ethyl acetate/hexane) to provide the desired product (m.p. 85-88° C.). Anal. Calcd. for C17H20N2O5.0.9H2O: C, 58.73; H, 6.29; N, 8.06; Found: C, 58.74; H, 5.91; N, 7.53.

Workup

  1. custombefore being quenched with saturated NaHS2O3 (2 mL)
  2. extractionto extract
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe residue after filtration and concentration
  5. customis chromatographed on silica ;gel (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4378e9e7fbe741038523fb9a073382f6
Source dataset
uspto-grants-2001_06
Patent number
US06245760B1

Reaction notes

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