Sodium borohydride → HCID 118389634, compound

HRID 1774604Notes

Reaction equation

HRID 1774604 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[C:12]([O:16][CH:17]([C:22]1[N:26]([CH3:27])[N:25]=[C:24]([C:28]2[CH2:33][CH2:32][CH2:31][C:30](=[O:34])[CH:29]=2)[C:23]=1[C:35]1[CH:36]=[CH:37][C:38]2[O:43][CH2:42][CH2:41][CH2:40][C:39]=2[CH:44]=1)[C:18]([O:20][CH3:21])=[O:19])([CH3:15])([CH3:14])[CH3:13].[BH4-].[Na+]>C(O)C>[C:12]([O:16][CH:17]([C:22]1[N:26]([CH3:27])[N:25]=[C:24]([C:28]2[CH2:33][CH2:32][CH2:31][CH:30]([OH:34])[CH:29]=2)[C:23]=1[C:35]1[CH:36]=[CH:37][C:38]2[O:43][CH2:42][CH2:41][CH2:40][C:39]=2[CH:44]=1)[C:18]([O:20][CH3:21])=[O:19])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 118389629HCID 118389629, compound

Product 1

HCID 118389634HCID 118389634, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Cerium(III) chloride heptahydrate (62 mg, 0.167 mmol) was added to a solution of methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(3-oxocyclohex-1-en-1-yl)-1H-pyrazol-5-yl]acetate (43c) (63 mg, 0.139 mmol) in ethanol (0.46 mL). The reaction mixture was cooled to 0° C. and sodium borohydride (6 mg, 0.167 mmol) was slowly added. After stirring for 1 hour at the same temperature, the reaction was quenched with water (2 mL) and concentrated in vacuo to remove ethanol. The resulting aqueous layer was extracted with ethyl acetate (2×2 mL). The organic layer was washed with brine (3 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (dichloromethane/ethyl acetate 50/50) to provide methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(3-hydroxycyclohex-1-en-1-yl)-1-methyl-1H-pyrazol-5-yl]acetate (43d) (55 mg, 0.121 mmol, 87%) as a mixture of diastereoisomers.

Workup

  1. customthe reaction was quenched with water (2 mL)
  2. concentrationconcentrated in vacuo
  3. customto remove ethanol
  4. extractionThe resulting aqueous layer was extracted with ethyl acetate (2×2 mL)
  5. washThe organic layer was washed with brine (3 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative TLC (dichloromethane/ethyl acetate 50/50)

Sources & evidence

ORD record
ord-d199b22e798741348134e705a46e30ce
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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