Acetonitrile → HCID 20824937, compound

HRID 853036Notes

Reaction equation

HRID 853036 reaction equation
[Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][NH:13][CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.[C:15](=[O:18])([O-])[O-].[K+].[K+].[C:21](#N)C>>[Br:1][C:2]1[C:3]2[CH2:4][C@@H:5]3[CH2:14][N:13]([CH2:21][CH2:15][OH:18])[CH2:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 69415545HCID 69415545, compound

Product 1

HCID 20824937HCID 20824937, compound

Procedure

(10aR)-9-Bromo-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (0.10 g, 0.39 mmol) and 2-(bromoethoxy)-tert-butyl-dimethylsilane (88 mg, 0.39 mmol) were dissolved in acetonitrile (2 mL). Potassium carbonate (63 mg, 0.46 mmol) was added and the solution was boiled with stirring for 2 d. The solvent was removed and the residue was partitioned between dichloromethane and brine. The organic phases were pooled, dried with MgSO4 and the solvent was evaporated. Chromatography on silica gel (dichloromethane/methanol 98:2) yielded the intermediate silyl-protected alcohol (124 mg, 76%), MS: m/e=413.3 (M+H+).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between dichloromethane and brine
  3. dry with materialdried with MgSO4
  4. customthe solvent was evaporated
  5. customChromatography on silica gel (dichloromethane/methanol 98:2) yielded the intermediate silyl-protected alcohol (124 mg, 76%), MS

Sources & evidence

ORD record
ord-8f0a70cec8c44ef78f1b55b3cd3536a1
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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