Sodium triacetoxyborohydride → HCID 21706143, compound

HRID 650918Notes

Reaction equation

HRID 650918 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH:15]=[O:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH2:15][OH:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 21706134HCID 21706134, compound

Product 1

HCID 21706143HCID 21706143, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 405.2 mg (1.8 mmol) of aldehyde prepared in Step G and 804.3 mg (3.8 mmol) of sodium triacetoxyborohydride in 27 mL of anhydrous THF was refluxed under nitrogen for 1 hour. The cooled mixture was partitioned between EtOAc, ice-water and saturated NaHCO3, and the organic phase was separated, washed with brine, dried over Na2SO4, filtered, evaporated, and dried in vacuo. Purification by PLC with CH2Cl2-EtOAc (2:1) yielded 303.7 mg of the crystalline, title product.

Workup

  1. temperaturewas refluxed under nitrogen for 1 hour
  2. customThe cooled mixture was partitioned between EtOAc, ice-water and saturated NaHCO3
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customPurification by PLC with CH2Cl2-EtOAc (2:1)

Sources & evidence

ORD record
ord-7c7877482135495b989b393b34f8d4b7
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

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