Ammonium Chloride → HCID 19696324, compound

HRID 475479Notes

Reaction equation

HRID 475479 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][N:5]12.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][N:5]12

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 15063399HCID 15063399, compound

Product 1

HCID 19696324HCID 19696324, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 8,9-dihydropyrido[1,2-α]indol-7(6H)-one from Step 6 in MeOH (0.3 M) was added NaBH4 (1 equiv.) portionwise. After stirring for 1 h at 0° C., the reaction mixture was poured into an equal volume of saturated aqueous solution of NH4Cl and extracted (2×) with EtOAc. The combined organic layers were washed with brine, dried with MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel using a CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hex (10:90 to 60:40) to give the title compound (98%) as a yellow solid.

Workup

  1. extractionextracted (2×) with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel using a CombiFlashRF (Teledyne ISCO)
  6. washeluting with EtOAc/Hex (10:90 to 60:40)

Sources & evidence

ORD record
ord-fedfc7c1db924c4da2f4f59502224921
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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