Sulfuric Acid → HCID 68691015, compound

HRID 1296230Notes

Reaction equation

HRID 1296230 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[C:12]([O:16][C:17]([N:19]1[CH2:36][CH2:35][N:22]2[C:23](=O)[C:24]3[C:29]([C@@H:21]2[CH2:20]1)=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])=[O:18])([CH3:15])([CH3:14])[CH3:13]>O1CCCC1>[C:12]([O:16][C:17]([N:19]1[CH2:36][CH2:35][N:22]2[CH2:23][C:24]3[C:29]([C@@H:21]2[CH2:20]1)=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:31])([F:32])[F:33])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 16115786HCID 16115786, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68691015HCID 68691015, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of lithium aluminum hydride (1.12 mL, 1.12 mmol; 1.0 M in THF) in dry tetrahydrofuran (1.2 mL) at 0° C. was added dropwise sulfuric acid (0.50 mL, 0.50 mmol; 1.0 M in THF). After 1 h, N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (100 mg, 0.28 mmol) was added dropwise as a solution in tetrahydrofuran (1.2 mL). The reaction was slowly allowed to warm to room temperature over a period of 1 h and was then quenched by the addition of water (2 mL) and 1N aqueous sodium hydroxide (0.30 mL). The mixture was extracted with ethyl acetate (×3), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated. The resulting pale yellow residue was purified by radial chromatography (30–50% ethyl acetate in hexanes) to afford N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-7-trifluoromethyl-pyrazino[2,1-a]isoindole (37 mg, 39%) as a clear residue. MS (ESI) 343.4 (M+H).

Workup

  1. customwas then quenched by the addition of water (2 mL) and 1N aqueous sodium hydroxide (0.30 mL)
  2. extractionThe mixture was extracted with ethyl acetate (×3)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting pale yellow residue was purified by radial chromatography (30–50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7b892a01734e47d783d556b50c75d45c
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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