Methyl morpholine oxide → HCID 86675858, compound

HRID 1895769Notes

Reaction equation

HRID 1895769 reaction equation
[CH3:1][O:2][C@H:3]([C@@H:8]([CH3:27])[C@@H:9]([O:25][CH3:26])/[CH:10]=[CH:11]/[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:4]([CH3:7])[CH2:5][OH:6].C[N+]1([O-])CCOCC1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][O:2][C@H:3]([C@@H:8]([CH3:27])[C@@H:9]([O:25][CH3:26])/[CH:10]=[CH:11]/[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[C@@H:4]([CH3:7])[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86675859HCID 86675859, compound

Product 1

HCID 86675858HCID 86675858, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To (E)-(2S,3S,4R,5R)-3,5-Dimethoxy-2,4-dimethyl-7-tributylstannanyl-hept-6-en-1-ol (100 mg, 0.2 mmol) in anhydrous dichloromethane (2 ml) at room temperature and under an atmosphere of nitrogen was added activated 4A molecular sieves (50 mg), N-methylmorpholine-N-oxide (71 mg, 0.61 mmol) and TPAP (3.6 mg, 0.01 mmol). The reaction was stirred for 30 minutes and filtered through a SiO2 pad, and the pad washed well with diethyl ether. The filtrate was concentrated in vacuo to afford the product as a clear oil (98 mg, 100%). 1H NMR (300 MHz, CDCl3) δ 9.74 (d, J=2.6 Hz, 1H), 6.08 (d, J=19.0 Hz, 1H), 5.58 (dd, J=19.0 Hz, 8.2 Hz, 1H), 3.77 (dd, J=9.1 Hz, 2.3 Hz, 1H), 3.34 (s, 3H), 3.25 (t, J=9.3 Hz, 1H), 3.18 (s, 3H), 2.54 (m, 1H), 1.59 (m, 1H), 1.44 (m, 6H), 1.24 (m, 6H), 0.93 (d, J=7.0 Hz, 3H), 0.82 (m, 15H), 0.75 (d, J=7.0 Hz, 3H).

Workup

  1. filtrationfiltered through a SiO2 pad
  2. washthe pad washed well with diethyl ether
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-35ba744812ff4818abee8e7bcf3026bf
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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