Dimethyl Sulfide → HCID 15341581, compound

HRID 1684534Notes

Reaction equation

HRID 1684534 reaction equation
[O:1]=[O+][O-].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]1[C:22](=[O:27])[O:23][C@@H:24]([CH:25]=C)[C@H:17]1[CH2:16][CH2:15]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[BH4-].[Na+].CSC>ClCCl.CO>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]1[C:22](=[O:27])[O:23][C@@H:24]([CH2:25][OH:1])[C@H:17]1[CH2:16][CH2:15]2)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 4311764Sodium borohydrideHCID 15341579HCID 15341579, compound

Product 1

HCID 15341581HCID 15341581, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

Ozone is sparged for 3 h 30 min into a solution of 12.5 g (0.039 mol) of trans-7-benzyloxy-3-ethenyl-3,3a,4,5-tetrahydro-1H-oxazolo[3,4-a]quinolin-1-one in 450 ml of dichloromethane and 350 ml of methanol, cooled to -40° C. The excess ozone is then stripped off with a stream of nitrogen, 14.8 g (0.39 mol) of sodium borohydride are added in small portions, followed by 12.6 g (0.195 mol) of dimethyl sulphide, and the mixture is left overnight at room temperature. It is extracted twice with dichloromethane, the organic phase is washed with water and then with saturated sodium chloride solution and dried, and the solvent is evaporated off under reduced pressure. After purification by chromatography on a column of silica, with a 95/5 mixture of dichloromethane and methanol, 10.9 g of product are obtained.

Workup

  1. additionare added in small portions
  2. extractionIt is extracted twice with dichloromethane
  3. washthe organic phase is washed with water
  4. dry with materialwith saturated sodium chloride solution and dried
  5. customthe solvent is evaporated off under reduced pressure
  6. customAfter purification by chromatography on a column of silica
  7. additionwith a 95/5 mixture of dichloromethane and methanol, 10.9 g of product
  8. customare obtained

Sources & evidence

ORD record
ord-7e9829413ad2483cb7b276be0214b0bd
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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