Hydrochloric Acid → HCID 68507183, compound

HRID 1714021Notes

Reaction equation

HRID 1714021 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[CH2:21][C:20](=O)[NH:19][CH2:18][C:17]4[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][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:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 68508583HCID 68508583, compound

Product 1

HCID 68507183HCID 68507183, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 14-cyclohexyl-3-fluoro-7-oxo-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate (from Step 4) in THF (0.02 M), BH3.THF (5 eq, 1 M solution in THF) was added and the solution stirred at RT for 2 h. MeOH (0.02 M) and a 1.25 M solution HCl in MeOH (0.24 M) were added carefully and left overnight to stir at RT before reducing the volume of the volatiles in vacuo and 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 407 (M+H)+.

Workup

  1. waitleft overnight
  2. stirringto stir at RT
  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-4926b62327864c689577014fafed8788
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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