Ethyl Acetate → HCID 86749596, compound

HRID 1733908Notes

Reaction equation

HRID 1733908 reaction equation
[C:1]([N:9]1[CH2:18][CH2:17][C@H:16]2[C@@H:11]([CH2:12][CH2:13][C:14]([OH:33])([C:19]3[CH:24]=[CH:23][C:22]([O:25][Si](C(C)(C)C)(C)C)=[CH:21][CH:20]=3)[CH2:15]2)[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C1COCC1>[CH2:1]([N:9]1[CH2:18][CH2:17][C@H:16]2[C@@H:11]([CH2:12][CH2:13][C:14]([OH:33])([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[CH2:15]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 131719445HCID 131719445, compound

Product 1

HCID 86749596HCID 86749596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trans-2-benzoyl-6-hydroxy-6-(4'-t-butyldimethylsilyloxyphenyl)decahydroisoquinoline (Example 48, 740 mg, 1.61 mmol) and lithium aluminum hydride (0.31 g, 8 mmol) in anhydrous THF (20 mL) was stirred at reflux temperature under a nitrogen atmosphere for 19.5 h. The reaction mixture was cooled to room temperature and quenched with excess ethyl acetate, followed by water (0.3 mL), a 1N NaOH solution (0.3 mL) and water (1 mL). The precipitate was filtered through celite; the filtrate was dried over magnesium sulfate and filtered. Removal of solvent in vacuo gave an oil. Column chromatography (ethyl acetate) gave the product, a solid (209 mg): mp 108°-109° C., NMR (CDCl3, 200 MHz): 7.4-7.2 (m, 7H), 6.8 (d, 2H, J=7), 3.55 (s, 2H), 2.95 (br d, 1H, J=8), 2.85 (br d, 1H, J=8), 2.2 (s, 2H), 2.1-1.2 (m, 11H); Anal. Calcd for C22H27NO2.O.3H2O: C, 77.06, H, 8.11, N, 4.09; Found C, 76.82, 76.83, H, 7.95, 8.15, N, 3.88, 3.80.

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere for 19.5 h
  2. customquenched with excess ethyl acetate
  3. filtrationThe precipitate was filtered through celite
  4. dry with materialthe filtrate was dried over magnesium sulfate
  5. filtrationfiltered
  6. customRemoval of solvent in vacuo
  7. customgave an oil

Sources & evidence

ORD record
ord-a8a22ddeab704e62a3e2b320ddaf1ab4
Source dataset
uspto-grants-1996_07
Patent number
US05532243

Reaction notes

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