3,4-dihydro-2-methoxycarbonyl-2H-(1,3)-thiazino-[3,2-a]benzimidazole → 3,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole

HRID 1164390Notes

Reaction equation

HRID 1164390 reaction equation
C[O:2][C:3]([CH:5]1[S:17][C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:3][CH:5]1[S:17][C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 128512483,4-dihydro-2-methoxycarbonyl-2H-(1,3)-thiazino-[3,2-a]benzimidazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 128523233,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazoleYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.48 g (10 m mole) of 3,4-dihydro-2-methoxycarbonyl-2H-(1,3)-thiazino-[3,2-a]benzimidazole in dry tetrahydrofuran (50 ml) was added dropwise 0.5 g of lithium aluminum hydride devided in small pieces, with stirring under ice cooling condition. After thirty minutes, the resultant complex was decomposed by the addition of hydrated tetrahydro furan and subjected to filtration. Subsequent to drying the filtrate over anhydrous magnesium sulfate, tetrahydrofuran was evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform to obtain 1.2 g (yield: 54.5%) of the intended product, m.p. 112°-113° C.;

Workup

  1. waitAfter thirty minutes
  2. filtrationsubjected to filtration
  3. dry with materialSubsequent to drying the filtrate over anhydrous magnesium sulfate, tetrahydrofuran
  4. customwas evaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-542ea406a2db425ca62f04095f6a1593
Source dataset
uspto-grants-1983_01
Patent number
US04369309

Reaction notes

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