Methyl {(7 R)-7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7-dihydro pyrido[1,2-alpha]indol-10-yl}acetate → Methyl {(7R)-7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-alpha] indol-10-yl}acetate

HRID 475497Notes

Reaction equation

HRID 475497 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:30])[C@H:12]2[CH2:29][N:16]3[C:17]4[C:22]([C:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:15]3[CH:14]=[CH:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:30])[C@H:12]2[CH2:29][N:16]3[C:17]4[C:22]([C:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:15]3[CH2:14][CH2:13]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58399168Methyl {(7 R)-7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7-dihydro pyrido[1,2-alpha]indol-10-yl}acetate

Product 1

HCID 58399160Methyl {(7R)-7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-alpha] indol-10-yl}acetateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl {(7R)-7-[[(4-fluorophenyl)sulfonyl](methyeamino]-6,7-dihydropyrido[1,2-α]indol-10-yl}acetate (1 equiv.) from step 7 in EtOAc (0.25 M) was added 10% Pd-C (20 mg/mmol) and the flask thoroughly purged with nitrogen. The stirring black solution was purged with hydrogen gas, then left under 1 atmosphere pressure of hydrogen and protected from light. The reaction was stirred for 24 h and then filtered through a plug of Celite 545, the plug was washed with EtOAc (2×), and the combined organics were concentrated under vacuum to give a yellow foam. Purification by column chromatography on silica gel using a CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hex (20:80 to 40:60) gave the title compound (91%) as a light yellow foam.

Workup

  1. customthe flask thoroughly purged with nitrogen
  2. customThe stirring black solution was purged with hydrogen gas
  3. waitleft under 1 atmosphere pressure of hydrogen
  4. filtrationfiltered through a plug of Celite 545
  5. washthe plug was washed with EtOAc (2×)
  6. concentrationthe combined organics were concentrated under vacuum
  7. customto give a yellow foam
  8. customPurification by column chromatography on silica gel using a CombiFlashRF (Teledyne ISCO)
  9. washeluting with EtOAc/Hex (20:80 to 40:60)

Sources & evidence

ORD record
ord-a709d17aad3943278567612fe4b8069f
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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