Sodium Hydroxide → HCID 9815913, compound

HRID 853039Notes

Reaction equation

HRID 853039 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]3[CH2:14][NH:13][CH2:12][C@@H:11]([CH3:15])[N:8]3[C:9]=2[CH:10]=1.[BH4-].[Na+].[OH-].[Na+]>O1CCCC1.FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@@H:7]3[CH2:14][NH:13][CH2:12][C@@H:11]([CH3:15])[N:8]3[C:9]=2[CH:10]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C@H:7]3[CH2:14][NH:13][CH2:12][C@@H:11]([CH3:15])[N:8]3[C:9]=2[CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 9815884HCID 9815884, compound

Product 2

HCID 9815913HCID 9815913, compoundYield 45%HCID 69414227HCID 69414227, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 18627201HCID 18627201, compoundSolvent

Conditions

Temperature
0 °C

Procedure

(4R)-7-Chloro-4-methyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole (0.180 g; 0.816 mmol) is dissolved in a tetrahydrofuran/trifluoroacetic acid mixture (1:2; 7.5 ml) and cooled to 0° C. Sodium borohydride (62 mg; 1.63 mmol) was added and the solution was stirred for 2 h. The reaction mixture was poured in an aqueous NaOH solution, basified to ph 14 and extracted twice with ethyl-acetate. Organic phases were pooled, dried with MgSO4 and the solvent was evaporated. Chromatography on silica gel (dichloromethane/methanol 9:1) gave (4R,10aR)-7-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (81 mg, 45%) and (4R,10aS)-7-chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (17 mg, 9%).

Workup

  1. extractionextracted twice with ethyl-acetate
  2. dry with materialdried with MgSO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2702b20f91e9441d9a21372d09f8a614
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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