Dichloromethane → HCID 69416895, compound

HRID 853054Notes

Reaction equation

HRID 853054 reaction equation
C(OC([N:8]1[CH2:25][CH:24]([CH3:26])[N:11]2[C:12]3[CH:13]=[C:14]([C:20]([F:23])([F:22])[F:21])[C:15]([Br:19])=[CH:16][C:17]=3[CH2:18][CH:10]2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+].[Cl:36]CCl>>[ClH:36].[Br:19][C:15]1[C:14]([C:20]([F:22])([F:23])[F:21])=[CH:13][C:12]2[N:11]3[C@H:24]([CH3:26])[CH2:25][NH:8][CH2:9][C@H:10]3[CH2:18][C:17]=2[CH:16]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69417569HCID 69417569, compound

Product 1

HCID 69416895HCID 69416895, compound

Procedure

8-Bromo-4-methyl-7-trifluoromethyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester (0.35 g, 0.8 mmol) were dissolved in dichloromethane (12 mL) and trifluoroacetic acid was added (3 mL). The mixture was stirred for 1 h, added to 1 N sodium hydroxide solution (50 mL) and extracted with dichloromethane (3×40 mL). Organic phases were pooled, washed with brine, dried with MgSO4 and the solvent was removed in vacuo. Chromatography on silica gel (dichloromethane/methanol 19:1) yielded the title compound as a colorless oil which was precipitated as HCl salt from diethylether (0.2 g; 73%). ISP-MS: m/e=335.2, 337.2 (M+H+), αD20=−48.6.

Workup

  1. extractionextracted with dichloromethane (3×40 mL)
  2. washwashed with brine
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b388eb47ccf943fc98e9786745fade78
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

Loading…