Hydrochloric Acid → Octahydropyrazino[2,1-c][1,4]thiazine 2,2-dioxide

HRID 421188Notes

Reaction equation

HRID 421188 reaction equation
[CH2:1]1[CH:6]2[C:7](=O)[NH:8][CH2:9][CH2:10][N:5]2[CH2:4][CH2:3][S:2]1(=[O:13])=[O:12].Cl>C1COCC1>[CH2:1]1[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[CH2:4][CH2:3][S:2]1(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59215885Hexahydropyrazino[2,1-c][1,4]thiazin-9(6H)-one 2,2-dioxide

Product 1

HCID 59215787Octahydropyrazino[2,1-c][1,4]thiazine 2,2-dioxideYield 111.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of hexahydropyrazino[2,1-c][1,4]thiazin-9(6H)-one 2,2-dioxide (D18; 165 mg, 0.81 mmol) in 1 ml of anhydrous THF were added successive aliquots of a 1M solution of borane THF complex in THF (total 20.4 ml, 20.4 mmol) and the reaction stirred at room temperature and 50° C., until disappearance of the starting material. Hydrochloric acid (5M, 2 ml) was added to the solution and stirring was continued at 50° C. for 12 h. The solvent was removed under reduced pressure and the residue loaded on a SCX cartridge, washed with methanol and eluted with 0.5M methanolic ammonia. The basic fractions were collected and the solvent removed leaving 172 mg of the target product, partially contaminated by the starting material.

Workup

  1. stirringstirring
  2. customThe solvent was removed under reduced pressure
  3. washwashed with methanol
  4. washeluted with 0.5M methanolic ammonia
  5. customThe basic fractions were collected
  6. customthe solvent removed

Sources & evidence

ORD record
ord-8693f89f92a5497c8a16b54b27cb445c
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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