Hydrochloric Acid → HCID 68501783, compound

HRID 1714052Notes

Reaction equation

HRID 1714052 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:22](=O)[C@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH3:28])[CH2:18][C:17]4[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1.Cl>C1COCC1.CO.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][C@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH3:28])[CH2:18][C:17]4[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 68506071HCID 68506071, compound

Product 1

HCID 68501783HCID 68501783, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 14-cyclohexyl-3-fluoro-6-(1-methyl-D-prolyl)-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate in THF (0.02 M), 3×5 eq of BH3.THF (1 M solution in THF) were added sequentially over a period of 48 h. The solution was allowed to stir at RT and monitored until no starting material was visible by RP-LC-MS. MeOH (0.02 M) and a 1.25 M solution of HCl in MeOH (0.24 M) were added carefully and the mixture heated at reflux for 2 h. The volume of the solution was reduced in vacuo, before diluting with EtOAc. The organic phase was washed with aqueous NaHCO3 solution and brine, before being dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound. The crude was used in the next step without further purification (quant); MS (ES+) m/z 504 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 h
  3. washThe organic phase was washed with aqueous NaHCO3 solution and brine
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5ab9e32548b34332bfd21306b002d321
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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