Methyl morpholine oxide → HCID 21864738, compound

HRID 966400Notes

Reaction equation

HRID 966400 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]1[CH2:12][CH:5]2C=C1.C[N+]1([O-])[CH2:19][CH2:18][O:17]CC1.[OH:21]S([O-])=O.[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]1[CH2:12][CH:5]2[CH:18]([OH:17])[CH:19]1[OH:21]

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 1435636-Fluoro-1,4-dihydro-1,4-methanonaphthaleneHCID 23665763Sodium Bisulfite

Product 1

HCID 21864738HCID 21864738, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

6-Fluoro-1,4-dihydro-1,4-methano-naphthalene (680 mg, 4.22 mmol) and N-methyl morpholine N-oxide (599 mg, 4 43 mmol) were stirred in acetone (50 mL) and H2O (5 mL). To this was added a solution of OsO4 (0.2 mL. 2.5% wt solution in t-BuOH, 0.02 mmol) After 72 hours, flonsil (5 g) and saturated aqueous NaHSO3 solution (3 mL) were added and stirred for 1 hour. The flonsil was filtered and the filtrate concentrated to produce a crystalline product which was triturated with acetone and filtered (524 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 7.10 (dd, J=8.0, 5.0 Hz, 1H), 6 90 (dd, J=8 0, 2.3 Hz, 1H), 6 75 (ddd, J=8 0, 8.0, 2.3 Hz, 1H), 3.79 (s, 2H), 3.18 (d, J=1 5 Hz, 2H), 2.22 (d, J=10 0 Hz, 1H), 1 92 (dd, J=10 0, 1.5 Hz, 1H) GCMS m/e 194 (M+)

Workup

  1. filtrationThe flonsil was filtered
  2. concentrationthe filtrate concentrated
  3. customto produce a crystalline product which
  4. customwas triturated with acetone
  5. filtrationfiltered (524 mg, 64%)

Sources & evidence

ORD record
ord-3449fbbc47354045ad9fdb326c542332
Source dataset
uspto-grants-2005_10
Patent number
US06951938B2

Reaction notes

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