Hydrochloric Acid → HCID 18963881, compound

HRID 257059Notes

Reaction equation

HRID 257059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11](=[O:13])(=[O:12])[N:10]([CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9](=O)[CH2:8][C:7]=2[CH:24]=1.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11](=[O:13])(=[O:12])[N:10]([CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:9][CH2:8][C:7]=2[CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18963924HCID 18963924, compound

Product 1

HCID 18963881HCID 18963881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 1M BH3 solution (300 mL, 30 mmol) @ 0° is added a solution of 6-methoxy-2-(3-phenylpropyl)-3-oxo-3,4-dihydro-2H-1,2-benzothiazine-1,1-dioxide (3.3 g, 9.6 mmol) in anhydrous THF (75 mL). After addition is complete the reaction mixture is brought to reflux for 2 hours. When the mixture has cooled to ambient temperature 6N HCl is carefully added until gas evolution ceases. The volatiles are removed in vacuo and the residue extracted with EtOAc (200 mL). The organic phase is washed with saturated NaCl solution (2×200 mL), dried over MgSO4 and concentrated in vacuo. The resulting material is chromatographed (silica gel, 1:2 EtOAc/hexanes) to afford 6-methoxy-2-(3-phenylpropyl)-3,4-dihydro-2H-1,2-benzothiazine-1,1-dioxide.

Workup

  1. additionAfter addition
  2. temperatureto reflux for 2 hours
  3. additionis carefully added until gas evolution ceases
  4. customThe volatiles are removed in vacuo
  5. extractionthe residue extracted with EtOAc (200 mL)
  6. washThe organic phase is washed with saturated NaCl solution (2×200 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe resulting material is chromatographed (silica gel, 1:2 EtOAc/hexanes)

Sources & evidence

ORD record
ord-c7187e2731c048edbd25323ad2fead3f
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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