Hydrochloric Acid → 2-(3-Methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxide

HRID 1736009Notes

Reaction equation

HRID 1736009 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]([C:12](OCC)=[O:13])=[CH:10][C:9]2[CH:17]=[CH:18][S:19][C:8]=2[S:7]1(=[O:21])=[O:20].CC(C[AlH]CC(C)C)C.Cl>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[CH:17]=[CH:18][S:19][C:8]=2[S:7]1(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 19434095Ethyl 2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 194341212-(3-Methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxideYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step B (3.70 g, 11.18 mmol) in anhydrous THF (50 mL) at ambient temperature under nitrogen was added DIBAL (50 mL of a 1.0 M solution, 50.0 mmol). After stirring for 4 h the reaction mixture was cooled (ice bath) and 2N HCl (100 mL) was added over a 10 min period. THF was evaporated and the aqueous mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4), filtered and evaporated to give a viscous oil (3.23 g), which was used in the next step without further purification.

Workup

  1. additionwas added over a 10 min period
  2. customTHF was evaporated
  3. extractionthe aqueous mixture was extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ebae6c9feb3f479280cc498d4aaf634b
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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