Tetrahydrofuran → HCID 117817929, compound

HRID 1772402Notes

Reaction equation

HRID 1772402 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH:20]([CH2:27][C:28]2([CH3:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:21]3=[O:26])[CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].C1COCC1>C(O)C>[C:13]([C:11]1[CH:10]=[C:9]([C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH:20]([CH2:27][C:28]2([CH3:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:21]3[OH:26])[CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[CH:12]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 117817964HCID 117817964, compound

Product 1

HCID 117817929HCID 117817929, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.32 g, 34.83 mmol, 1.5 equiv) was added in portions at 0° C. to a solution of compound 13 (10.0 g, 23.22 mmol, 1.0 equiv), THF (100 mL) and ethanol (100 mL). The reaction mixture was stirred at room temperature overnight, when LCMS indicated that the reaction was complete. The mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate (300 mL) and water (50 mL). 1M 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 the crude compound 14 (10.0 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) and water (50 mL)
  3. addition1M 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-251ae77e804041c9b0907a31658ce1ed
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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