Water → HCID 69414127, compound

HRID 853057Notes

Reaction equation

HRID 853057 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:25][C@@H:24]([CH3:26])[N:11]2[C:12]3[CH:13]=[C:14]([C:20]([F:23])([F:22])[F:21])[C:15](Br)=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27]I.C[Li].O>C(OC)(C)(C)C.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:25][C@@H:24]([CH3:26])[N:11]2[C:12]3[CH:13]=[C:14]([C:20]([F:23])([F:22])[F:21])[C:15]([CH3:27])=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 69417911HCID 69417911, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 69414127HCID 69414127, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

(4R,10aR)-8-Bromo-4-methyl-7-trifluoromethyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester (0.38 g, 0.8 mmol) and methyl iodide (0.25 g, 1.6 mmol) were dissolved in tert-butylmethylether (3 mL). A solution of methyl lithium in diethylether (0.66 mL, 1.6 M) was added with cooling (0° C.) and stirring. The mixture was stirred for ½ h at 0° C., water (25 mL) was added and the mixture was extracted with diethylether (2×20 mL). Organic phases were pooled, dried with MgSO4 and the solvent was removed in vacuo. Chromatography on silica gel (n-hexane/diethylether 4:1) yielded the title product as light yellow oil (0.20 g, 63%).

Workup

  1. stirringThe mixture was stirred for ½ h at 0° C.
  2. extractionthe mixture was extracted with diethylether (2×20 mL)
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-153ef33810de4f4eab65d3ade800ad2a
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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