Sodium borohydride → HCID 58355110, compound

HRID 1509569Notes

Reaction equation

HRID 1509569 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]([C:26]([N:28]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@@H:29]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:32][C@H:31]([C:42](OC)=[O:43])[CH2:30]2)=[O:27])[N:15]=[N:14]1>C(O)C.C(=O)([O-])O.[Na+]>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:16]([C:26]([N:28]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@H:29]2[CH2:30][C@@H:31]([CH2:42][OH:43])[CH2:32][N:33]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[CH2:34]2)=[O:27])[N:15]=[N:14]1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 58355374HCID 58355374, compound

Product 1

HCID 58355110HCID 58355110, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Calcium(II) chloride (200 mg) was dissolved in ethanol (5 ml), sodium tetrahydroborate (140 mg) was added under ice-cooling and the mixture was stirred at 0° C. for 30 min. A solution (8 ml) of 1-tert-butyl 3-methyl (3R,5S)-5-[{[1-(2-fluorophenyl)-5-(phenoxymethyl)-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (760 mg) in ethanol was added to the reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 13 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-75:25) was concentrated under reduced pressure to give the object product (447 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 13 hr
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. washa fraction eluted with ethyl acetate-hexane (5:95-75:25)
  9. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-70786fc114f8413e96f9aad23fa5078a
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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