HCID 21712792, compound → HCID 21712758, compound

HRID 650597Notes

Reaction equation

HRID 650597 reaction equation
[CH2:1]([N:5]1[C:10](=O)[CH2:9][S:8][C:7]2[S:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:6]1=2)[CH2:2][CH2:3][CH3:4]>O1CCCC1>[CH2:1]([N:5]1[CH2:10][CH2:9][S:8][C:7]2[S:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:6]1=2)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 21712792HCID 21712792, compound

Product 1

HCID 21712758HCID 21712758, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-n-butyl-2,3-dihydro-6-methoxycarbonyl-2-oxo-1H-thieno[2,3-b][1,4]thiazine (31.9 g) in tetrahydrofuran (300 ml) was added dropwise boran-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran) (294 ml). After stirring for 3 hours at room temperature, the solvent was evaporated in vacuo and the residue was poured into water. The solution was adjusted to pH 8 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with toluene. The fractions containing the object compound were collected and evaporated in vacuo to give 1-n-butyl-2,3-dihydro-6-methoxycarbonyl-1H-thieno-[2,3-b][1,4]thiazine (30.85 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionthe residue was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography on silica gel eluting with toluene
  8. additionThe fractions containing the object compound
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-c47e83ae9ed0475e899f00187de9bc73
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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