Methanol → HCID 68689285, compound

HRID 1296277Notes

Reaction equation

HRID 1296277 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][N:11]2[C:12](=[O:23])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][C:14]=3SC)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[O:27][S:28]([O-:30])=O.[K+].[CH3:32]O>O>[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][N:11]2[C:12](=[O:23])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][C:14]=3[S:28]([CH3:32])(=[O:30])=[O:27])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 68690390HCID 68690390, compound

Product 1

HCID 68689285HCID 68689285, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-ethyl-7-methylthio-pyrazino[2,1-a]isoindol-6(2H)-one (42 mg, 0.12 mmol) in dry MeOH (0.75 mL) and water (0.75 mL) was added oxone (93 mg, 0.15 mmol). The reaction was stirred for 4 h and then diluted with water. The reaction was extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc in vacuo to a yellow oil. The oil was purified by flash chromatography (SiO2, 0–50% EtOAc in hexanes) to yield 38 mg (84%) of the product as a colorless oil. MS (ESI) 395 (M+H).

Workup

  1. extractionThe reaction was extracted with EtOAc (3×5 mL)
  2. dry with materialdried over Na2SO4
  3. customThe oil was purified by flash chromatography (SiO2, 0–50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-415555729d7c4a6fadda1b207844eabc
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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