Ethyl Acetate → HCID 20672302, compound

HRID 1386792Notes

Reaction equation

HRID 1386792 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH:15]1([C@@H:19]([CH3:28])[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[CH2:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1>[C:22]1([C@H:20]([OH:21])[C@@H:19]([CH:15]2[CH2:18][CH2:17][CH2:16]2)[CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 3611392Lithium tri-s-butylborohydrideHCID 20672417HCID 20672417, compound

Product 1

HCID 20672302HCID 20672302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A dry flask was charged with 25 mL THF and a solution of L-Selectride® (12.6 mL, 1 M in THF, 12.6 mmol) was added. The solution was cooled to −78 C and a solution of (R)-Cyclobutylpropiophenone (2.38 grams, 12.6 mmol, from Step E) in 5 mL THF was added. After stirring at −78 C for 1 h the was warmed to room temperature gradually overnight. Sat'd sodium bicarbonate was added and the mixture was extrated with ethyl acetate. The organic portion was washed with water and sat'd NaCl. The solvent was removed and the residue was dissolved in methanol (100 mL). Concentrated HCl (1 mL) was added and the mixture was stirred at 50 C for 15 hours. After removal of the solvent the product was purified by flash chromatography (100/1 hexane/ethyl acetate →20/1 hexane ethyl acetate) to afford 1.4 grams (58%/o) of product. 1H NMR (500 MHz, CDCl3). δ 0.68 (d, 3H), 1.64-1.98 (m, 6H), 2.02-2.09 (m, 1H), 2.11-2.19 (m, 1H), 4.58 (d, 1H), 7.23-7.38 (m, 5H).

Workup

  1. temperatureThe solution was cooled to −78 C
  2. washThe organic portion was washed with water
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in methanol (100 mL)
  5. additionConcentrated HCl (1 mL) was added
  6. stirringthe mixture was stirred at 50 C for 15 hours
  7. customAfter removal of the solvent the product
  8. customwas purified by flash chromatography (100/1 hexane/ethyl acetate →20/1 hexane ethyl acetate)
  9. customto afford 1.4 grams (58%/o) of product

Sources & evidence

ORD record
ord-bb910a9021f5419c97cbc77acddef0f2
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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