Sodium borohydride → HCID 59407793, compound

HRID 2406035Notes

Reaction equation

HRID 2406035 reaction equation
C([O:3][C:4](=O)[C:5]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:6](OCC)=[O:7])C.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C.O1CCCC1.O>[C:24]([O:23][C:21](=[O:22])[NH:20][C:5]([CH2:4][OH:3])([CH2:6][OH:7])[CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57704533HCID 57704533, compound

Product 1

HCID 59407793HCID 59407793, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 21-1 (50.0 g) was dissolved in a mixture of ethanol (530 ml), tetrahydrofuran (130 ml) and water (260 ml). Calcium chloride (27.5 g) was added to this solution at 0° C., sodium borohydride (18.8 g) was subsequently added in portions, and the mixture was stirred at the same temperature for 2 hr, and further at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, added to saturated aqueous ammonium chloride solution (31), and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography to give the object product (21.6 g) as a colorless oil.

Workup

  1. waitfurther at room temperature for 18 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionadded to saturated aqueous ammonium chloride solution (31)
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1b1ec654b54b43959371118a0cecc7f4
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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