Ethyl Acetate → HCID 57466765, compound

HRID 2120333Notes

Reaction equation

HRID 2120333 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@@H:7]1[CH2:15][C@@H:10]2[O:11][C:12](=[O:14])[CH2:13][C@@H:9]2[C@H:8]1[CH2:16][CH2:17][C@@H:18]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:5])[CH3:2].CC(C[AlH]CC(C)C)C.C(OCC)(=O)C.C([O-])(=O)C(C(C([O-])=O)O)O.[Na+].[K+]>C1COCC1>[CH2:1]([O:3][CH:4]([O:6][C@@H:7]1[CH2:15][C@@H:10]2[O:11][CH:12]([OH:14])[CH2:13][C@@H:9]2[C@H:8]1[CH2:16][CH2:17][C@@H:18]([O:27][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 57466764HCID 57466764, compound

Product 1

HCID 57466765HCID 57466765, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3aR,4R,5R,6aS)-5-(1-Ethoxyethoxy)-4-[(3R)-3-(1-ethoxyethoxy)-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2-one (X, EXAMPLE 6) is dissolved in THF (14 mL) and the mixture cooled to −40°. Using a syringe pump, DIBAL (1.0 M, 3.78 mL in toluene) is added over 15 minutes, maintaining the internal temperature at less than −30°. The mixture is stirred for 15 minutes after the completion of the addition, then ethyl acetate (0.38 mL) is added. The mixture is poured into a solution of potassium sodium tartarate (10 g in 30 mL of water) and warmed to 20-25°. The two phase mixture is heated to 45° for 1 hr and then cooled. The phases are separated and the organic phase is concentrated.

Workup

  1. temperaturethe mixture cooled to −40°
  2. additionis added over 15 minutes
  3. temperaturemaintaining the internal temperature at less than −30°
  4. additionafter the completion of the addition
  5. temperaturewarmed to 20-25°
  6. temperatureThe two phase mixture is heated to 45° for 1 hr
  7. temperaturecooled
  8. customThe phases are separated
  9. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-ed695ee6d52b4292aa4e2afdbdd4fd0d
Source dataset
uspto-grants-2004_02
Patent number
US06689901B2

Reaction notes

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