Sodium borohydride → HCID 68755830, compound

HRID 1912524Notes

Reaction equation

HRID 1912524 reaction equation
[CH3:1][C:2]1([CH3:16])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][C@H:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]2=[O:9].[BH4-].[Na+]>CCO>[OH:9][CH:6]1[C@@H:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C@H:3]2[CH2:8][C@@H:7]1[C:2]2([CH3:1])[CH3:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11424625HCID 11424625, compound

Product 1

HCID 68755830HCID 68755830, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of Example 23A (0.62 g, 2.8 mmol) in EtOH (20 mL) was added sodium borohydride (0.13 g, 3.3 mmol) in portions at 0° C. The mixture was stirred at 0° C. for 4 hours and at room temperature overnight. The reaction mixture was then cooled, quenched with 1M NaHCO3, extracted with dichloromethane (3×15 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 0-30% of ethyl acetate in hexanes) to obtain 0.35 g of the title compound. MS (DCI/NH3) m/z 244 (M+NH4)+

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customquenched with 1M NaHCO3
  3. extractionextracted with dichloromethane (3×15 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (SiO2, 0-30% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9e826808a087417b8d34a770e584b5e8
Source dataset
uspto-grants-2013_12
Patent number
US08609674B2

Reaction notes

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