Lithium borohydride → HCID 18670501, compound

HRID 1059310Notes

Reaction equation

HRID 1059310 reaction equation
[C:1]([C:3]1[C:8]2[S:9][C:10]3[CH:19]=[CH:18][C:17]([C:20](OC)=[O:21])=[CH:16][C:11]=3[N:12]([CH2:13][O:14][CH3:15])[C:7]=2[N:6]=[CH:5][CH:4]=1)#[N:2].[BH4-].[Li+]>O1CCCC1>[C:1]([C:3]1[C:8]2[S:9][C:10]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:11]=3[N:12]([CH2:13][O:14][CH3:15])[C:7]=2[N:6]=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 18670491HCID 18670491, compound

Product 1

HCID 18670501HCID 18670501, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.19 g of methyl 4-cyano-10-(methoxymethyl)-10H-pyrido[3,2-b][1,4]-benzothiazine-8-carboxylate in dry tetrahydrofuran (5 ml) was added in a nitrogen atmosphere a solution of 0.026 g of lithium borohydride in tetrahydrofuran (10 ml) and the resulting mixture was heated under reflux for 20 minutes. After bringing back to room temperature, the mixture was extracted with 15 ml of water and 15 ml of acetic acid and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.12 g of the title compound as a pale yellow solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 20 minutes
  3. customAfter bringing back to room temperature
  4. extractionthe mixture was extracted with 15 ml of water and 15 ml of acetic acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-b50746445fd84d64afb7551592ff500b
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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