Sodium Hydroxide → (3,4-Dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methanol

HRID 1271700Notes

Reaction equation

HRID 1271700 reaction equation
O=[C:2]1[CH2:7][S:6][C:5]2[CH:8]=[CH:9][C:10]([C:12](OC)=[O:13])=[N:11][C:4]=2[NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCOCC.C(Cl)(Cl)Cl>[S:6]1[CH2:7][CH2:2][NH:3][C:4]2[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:5]1=2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 21873660Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

Product 1

HCID 18454501(3,4-Dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methanolYield 59.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (31a) (1.0 g) in dry tetrahydrofuran (170 ml) was treated with a 1M solution of lithium aluminium hydride in ether (14 ml) and the mixture was heated under reflux for 18 hours. It was cooled and a slight excess of 2N sodium hydroxide was added followed by chloroform and anhydrous sodium sulphate and the mixture was stirred for 30 minutes and filtered. The solution was evaporated to dryness to give a semi-solid (0.482 g)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureIt was cooled
  4. filtrationfiltered
  5. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-1bb47c27b74a49458f9b036fa092ce4e
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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