Ammonium Chloride → HCID 57861260, compound

HRID 1518089Notes

Reaction equation

HRID 1518089 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([C@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22]2[C:31]([CH:32]=[O:33])=[CH:30][C:29]3[C:24](=[CH:25][C:26]([F:35])=[C:27]([F:34])[CH:28]=3)[N:23]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.C1COCC1.[BH4-].[Na+].[NH4+].[Cl-]>C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([C@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22]2[C:31]([CH2:32][OH:33])=[CH:30][C:29]3[C:24](=[CH:25][C:26]([F:35])=[C:27]([F:34])[CH:28]=3)[N:23]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 57861236HCID 57861236, compound

Product 1

HCID 57861260HCID 57861260, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A crude 2-((R)-2-{4-[2-(benzyloxy)ethyl]cyclohexyl}pyrrolidin-1-yl)-6,7-difluoroquinoline-3-carbaldehyde is dissolved with ethanol-THF (120 mL/20 mL) and treated with sodium borohydride (1.33 g, 36 mmol) at 5° C., and the resulting mixture is stirred at the same temperature for 30 min. After addition of sat. NH4Cl aq. and ethyl acetate, the mixture is partially concentrated to remove ethanol. The mixture is extracted with EtOAc, and the organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give [2-((R)-2-{4-[2-(benzyloxy)ethyl]cyclohexyl}pyrrolidin-1-yl)-6,7-difluoroquinolin-3-yl]methanol as a yellow syrup.

Workup

  1. concentrationthe mixture is partially concentrated
  2. customto remove ethanol
  3. extractionThe mixture is extracted with EtOAc
  4. washthe organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4890526aa9fa4e0da9d57e6d21bd2922
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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