Methyl morpholine oxide → HCID 58359316, compound

HRID 870027Notes

Reaction equation

HRID 870027 reaction equation
[CH2:1]([Si:3]([CH2:17][CH3:18])([CH2:15][CH3:16])[O:4][C@@H:5]1[C@@H:12]([CH2:13][OH:14])[O:11][CH2:10][CH2:9][C@@:6]21[O:8][CH2:7]2)[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:15]([Si:3]([CH2:1][CH3:2])([CH2:17][CH3:18])[O:4][C@@H:5]1[C@@H:12]([CH:13]=[O:14])[O:11][CH2:10][CH2:9][C@@:6]21[O:8][CH2:7]2)[CH3:16]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58359314HCID 58359314, compound

Product 1

HCID 58359316HCID 58359316, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of alcohol 34 (15 mg, 0.05 mmol) and 4A° MS (15 mg) in CH2Cl2 (1 mL) at 0° C. was treated sequentially with N-methylmorpholine-N-oxide (9.6 mg, 0.08 mmol) and tetrapropylammonium perruthenate (1.9 mg, 5.47 μmol). After 10 min at 0° C., the resulting suspension was allowed to warm to room temperature and stirred for 30 min by which time TLC showed that all of starting material has been consumed. The suspension was directly loaded onto silica column and eluted with 40% ethyl acetate in hexane to give 7 mg (47%) of 35 as liquid. 1H NMR (400 MHz, CDCl3) δ 9.76 (d, J=0.9 Hz, 1H), 4.16 (ddd, J=11.5, 5.0, 2.7 Hz, 1H), 3.95-3.76 (m, 2H), 3.65 (td, J=11.5, 2.6 Hz, 1H), 3.05 (dd, J=5.3, 1.4 Hz, 1H), 2.59 (d, J=5.4 Hz, 1H), 2.21-2.07 (m, 1H), 1.59 (t, J=2.6 Hz, 1H), 0.98-0.89 (m, 10H), 0.66-0.55 (m, 6H).

Workup

  1. customhas been consumed
  2. washeluted with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3507edfc7f854c8096e28eae95aefb3f
Source dataset
uspto-grants-2015_03
Patent number
US08969405B2

Reaction notes

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