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Methyl10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylate → 10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine-8-methanol

HRID 1059275
Notes
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Reaction equation

HRID 1059275 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:14](OC)=[O:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:18]=[CH:19][CH:20]=[N:21][C:5]1=2.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:18]=[CH:19][CH:20]=[N:21][C:5]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11472176Methyl10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 1126581710-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine-8-methanolYield 78.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344Dichloromethane
Solvent

Procedure

Into a solution of 350 g of methyl 10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylate in methylene chloride (2.5 l) was added dropwise under a nitrogen atmosphere 3.2 l of a 1.01 M solution of diisobutylaluminum hydride in toluene while maintaining the system at a temperature not exceeding 15° C. Then the reaction mixture was poured into ice and stirred for 1 hour. After filtering off the insoluble matter, the filtrate was washed with water. After distilling off the solvent under reduced pressure, the crude crystals thus obtained were washed with diisopropyl ether to thereby give 250 g of the title compound as pale yellow crystals.

Workup

  1. temperaturewhile maintaining the system at a temperature not
  2. customexceeding 15° C
  3. additionThen the reaction mixture was poured into ice
  4. filtrationAfter filtering off the insoluble matter
  5. washthe filtrate was washed with water
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe crude crystals thus obtained
  8. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-87a29f1adeb04f6f9b3bd44ca5e953f6
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06518423B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes