Water → 10H-Pyrazino[2,3-b][1,4]benzothiazine-8-methanol

HRID 1059272Notes

Reaction equation

HRID 1059272 reaction equation
[H-].[Li+].[Al+3].[Li+].[H-].[H-].[H-].[H-].[N:9]1[C:18]2[NH:17][C:16]3[CH:19]=[C:20]([C:23](OC)=[O:24])[CH:21]=[CH:22][C:15]=3[S:14][C:13]=2[N:12]=[CH:11][CH:10]=1.O.[OH-].[Na+]>O1CCCC1>[N:9]1[C:18]2[NH:17][C:16]3[CH:19]=[C:20]([CH2:23][OH:24])[CH:21]=[CH:22][C:15]=3[S:14][C:13]=2[N:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11747308methyl 10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylateHCID 18670308Lithium aluminum lithium hydride

Product 1

HCID 1094429210H-Pyrazino[2,3-b][1,4]benzothiazine-8-methanolYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a solution of 40 g of lithium aluminum lithium hydride in tetrahydrofuran (1 l) was dropped a solution of 200 g of methyl 10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylate in tetrahydrofuran (2.5 l) while maintaining the mixture at a temperature not exceeding 15° C. After continuing the reaction at 15° C. or below for 1 hour, 40 ml of water, 40 ml of a 15% aqueous solution of sodium hydroxide and 120 ml of water were successively added and the resulting mixture was stirred for an additional 1 hour. After filtering off the insoluble matter, the solvent was distilled off under reduced pressure to thereby give 125 g of the title compound as yellow crystals.

Workup

  1. temperaturewhile maintaining the mixture at a temperature not
  2. customexceeding 15° C
  3. customthe reaction at 15° C. or below for 1 hour
  4. filtrationAfter filtering off the insoluble matter
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0ea0ec49df8b4a38b307025b56fa3dcc
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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