Sodium borohydride → HCID 23731075, compound

HRID 493903Notes

Reaction equation

HRID 493903 reaction equation
C([O:4][C:5]12[CH2:17][CH:13]([O:14][C:15]1=[O:16])[C:12]1[CH:7]([O:8][CH2:9][CH2:10][CH:11]=1)[CH2:6]2)(=O)C.[BH4-].[Na+]>[Cl-].[Na+].O>[OH:16][CH2:15][C@:5]1([OH:4])[CH2:6][C@@H:7]2[C:12](=[CH:11][CH2:10][CH2:9][O:8]2)[C@H:13]([OH:14])[CH2:17]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 74111316HCID 74111316, compound

Product 1

HCID 23731075HCID 23731075, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of tricyclic compound 8 (9.5 mg, 40 μmol) at 0° C. was added NaBH4. The resultant mixture was then stirred at room temperature for 18 h, a small volume of brine/saturated NH4Cl was added, and the solvents were removed in vacuum. The residue was washed several times with warm ethanol. The ethanol extracts were combined and evaporated to dryness with benzene. The solid residue was then washed few times with warm chloroform. The combined chloroform extracts were concentrated to a small volume and applied on a silica Sep-Pak cartridge. Elution with hexane/ethyl acetate (1:9, 20 mL) yielded a pure semisolid triol 9 (6 mg, 75%).

Workup

  1. customthe solvents were removed in vacuum
  2. washThe residue was washed several times with warm ethanol
  3. customevaporated to dryness with benzene
  4. washThe solid residue was then washed few times with warm chloroform
  5. concentrationThe combined chloroform extracts were concentrated to a small volume
  6. washElution with hexane/ethyl acetate (1:9, 20 mL)

Sources & evidence

ORD record
ord-10e3aba241044c10a4a91364c6821875
Source dataset
uspto-grants-2009_05
Patent number
US07538098B2

Reaction notes

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