Triethylborane → HCID 131715945, compound

HRID 1761975Notes

Reaction equation

HRID 1761975 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:22]=[CH:23][CH:24]([OH:34])[CH2:25][C:26](=[O:33])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:10]([CH:19]([CH3:21])[CH3:20])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(B(CC)CC)C.[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH:22]=[CH:23][CH:24]([OH:34])[CH2:25][CH:26]([OH:33])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:10]([CH:19]([CH3:21])[CH3:20])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7357TriethylboraneHCID 4311764Sodium borohydrideHCID 131715944HCID 131715944, compound

Product 1

HCID 131715945HCID 131715945, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.5 g of the title product of Step 4, above, in 100 ml of THF was added 12 ml of a 1.0 m solution of triethylborane in THF. After stirring at R.T. for 3 hours, the mixture was cooled to -78°, then 450 mg of sodium borohydride was added. The mixture was stirred at -78° for 24 hours. The reaction was then quenched with saturated aq. ammonium chloride solution, and extracted twice with MTBE. The extracts were combined and solvent was removed under reduced pressure to obtain a residue. The residue dissolved in 100 ml of methanol. After stirring at R.T. for 24 hours, the solvent was removed under reduced pressure and the resulting residue was flash chromatographed using 1% methanol/methylene chloride to elute the product, yielding 2.4 g of the title product of this example. (HPLC indicated an erythro:threo mixture of 82.3:17.7). Recrystallization of the product from cyclohexane increased the ratio to 88.3:11.7; m.p.=123°-125° .

Workup

  1. temperaturethe mixture was cooled to -78°
  2. stirringThe mixture was stirred at -78° for 24 hours
  3. customThe reaction was then quenched with saturated aq. ammonium chloride solution
  4. extractionextracted twice with MTBE
  5. customsolvent was removed under reduced pressure
  6. customto obtain a residue
  7. stirringAfter stirring at R.T. for 24 hours
  8. customthe solvent was removed under reduced pressure
  9. customchromatographed
  10. washto elute the product

Sources & evidence

ORD record
ord-4cf9ac17892049f18a6321383180613f
Source dataset
uspto-grants-1989_05
Patent number
US04829081

Reaction notes

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