Sodium Bicarbonate → HCID 12634676, compound

HRID 990791Notes

Reaction equation

HRID 990791 reaction equation
[CH:1]12[CH2:10][CH:5]([CH2:6][C:7](=[O:9])[CH2:8]1)[CH2:4][C:3](=[O:11])[CH2:2]2.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[C:7]12([OH:9])[CH2:8][CH:1]3[CH2:10][CH:5]([CH2:4][CH:3]([CH2:2]3)[O:11]1)[CH2:6]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 643315bicyclo[3.3.1]nonane-3,7-dioneHCID 4311764Sodium borohydride

Product 1

HCID 12634676HCID 12634676, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

386.6 mg (2.54 mmoles) of bicyclo[3.3.1]nonane-3,7-dione is dissolved in 5 mL of methanol and treated with sodium borohydride (100 mg, 2.64 mmoles) at 0° C. for 2 hours. The solution is treated with 5 mL of saturated aqueous sodium bicarbonate for 1 hour at 25° C. and extracted with 3×10 mL portions of chloroform. The combined chloroform extracts are combined, dried over sodium sulfate, stripped of solvent in vacuo, and purified by column chromatography (silica, eluant=50% hexanes, 50% ethyl acetate) yielding 343 mg (88%) of the desired product. 1HNMR (CDCl3, 500 Mhz): d 1.563 (d, 2H), 1.70-1.76 (m, 1H), 1.788 (d, 2H, J=11.1 Hz), 1.839 (d, 2H, J=13.1 Hz), 1.925 (d, 2H, J=13.0 Hz), 2.310 (s, 2H), 2.690 (s, 1H), 4.283 (s, 1H).

Workup

  1. extractionextracted with 3×10 mL portions of chloroform
  2. dry with materialdried over sodium sulfate
  3. custompurified by column chromatography (silica, eluant=50% hexanes, 50% ethyl acetate)

Sources & evidence

ORD record
ord-7c501bb625c649fe899d781451aba875
Source dataset
uspto-grants-2002_10
Patent number
US06462064B1

Reaction notes

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