Sodium borohydride → HCID 117817968, compound

HRID 1772404Notes

Reaction equation

HRID 1772404 reaction equation
[BH4-].[Na+].[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH:12]([CH3:19])[C:13]2=[O:18]>C1COCC1.C(O)C>[C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH:12]([CH3:19])[CH:13]2[OH:18]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22173138HCID 22173138, compound

Product 1

HCID 117817968HCID 117817968, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (2.34 g, 61.76 mmol, 1.5 equiv) was added in portions to a cold solution (0° C.) of compound 17 (12.27 g, 41.17 mmol, 1.0 equiv) in THF (125 mL) and ethanol (125 mL). The reaction mixture was stirred at room temperature for 2 hours when LC/MS indicated that the reaction was complete. The mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate (300 mL). 1 M HCl was added dropwise to quench the reaction. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated brine (500 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give crude compound 18 (13.0 g, >99% yield) as a pale-yellow oil. This material was used subsequently.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (300 mL)
  3. addition1 M HCl was added dropwise
  4. customto quench
  5. customthe reaction
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  8. washThe combined organic layers were washed with saturated brine (500 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59a240173916450eaf53f3308eea98d3
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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