Water → HCID 68576793, compound

HRID 639515Notes

Reaction equation

HRID 639515 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)=[CH2:2].[OH2:27].C[N+]1([O-])CC[O:32]CC1.[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O.C(OCC)(=O)C>[OH:27][CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)[CH2:2][OH:32]

Participants

8

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 68576452HCID 68576452, compound

Product 1

HCID 68576793HCID 68576793, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-vinyl-N-(tert-butyloxycarbonyl)morphinan 44 (10.5 mg, 0.03 mmol) in acetone:water=2:1 solution (0.3 mL) were added N-methylmorpholine-N-oxide (10 μL, 50 wt. % in water), and osmium tetroxide (one drop) sequentially and the mixture was stirred for 2 h at rt. After starting material disappeared on TLC, ethyl acetate (2 mL) and aqueous Na2SO3 solution (2 mL) were poured into the mixture, and the organic layer was separated, dried over MgSO4, and concentrated. Column chromatography gave 10 mg (87%) of the title compound: 1H NMR (300 MHz, CDCl3) δ7.29˜7.36 (1H, m); 7.17˜7.10 (2H, m); 4.79 (1H, d); 4.37 (0.55H, br); 4.19 (0.45H, br); 3.77˜3.66 (3H, m); 3.11 (1H, m); 2.72˜2.41 (4H, m); 2.03 (1H, m); 1.71˜1.04 (19H, m).

Workup

  1. additionwere poured into the mixture
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4a77f90081542bfbb19427f8644570a
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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