Aluminium lithium hydride → HCID 66694748, compound

HRID 1733902Notes

Reaction equation

HRID 1733902 reaction equation
[C:1]([N:9]1[CH2:18][CH2:17][C@H:16]2[C@@H:11]([CH2:12][CH2:13][C:14]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([OH:19])[CH2:15]2)[C:10]1=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:9]1[CH2:18][CH2:17][C@H:16]2[C@@H:11]([CH2:12][CH2:13][C:14]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)([OH:19])[CH2:15]2)[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86749591HCID 86749591, compound

Product 1

HCID 66694748HCID 66694748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-2-benzoyl-6-(4'-fluorophenyl)-6-hydroxydecahydroisoquinolone (76 mg, 2.16 mmol) in anhydrous THF (20 mL) was added dropwise to a stirred suspension of lithium aluminum hydride (95%, 0.49 g, 12.9 mmol) in anhydrous THF (20 mL) under a nitrogen atmosphere. The reaction mixture was then heated to reflux temperature and stirred for 23.5 h. The reaction was cooled to ambient temperature, quenched with an excess amount of ethyl acetate, followed by water (0.5 mL), a 2N NaOH solution (0.5 mL) and water (1.5 mL). The mixture was filtered through Celite. The filtrate was dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (ethyl acetate or CHCl3 ::MeOH::9:1) gave the product, a solid (382 mg): mp 120°-122° C.; NMR (CDCl3, 300 MHz): 7.45 (2H, dd, J=8, 6), 7.4-7.2 (m, 5H), 7.0 (br t, 2H, J=7), 3.55 (s, 2H), 2.95 (br d, 1H, J=7), 2.85 (br d, 1H, J=7), 2.05 (br t, 1H, J=7), 1.9-1.2 (m, 12H); HRMS: Calcd: 339.1999, Found: 339.2001; Anal. Calcd for C22H26FNO: C, 77.84, H, 7.72, N, 4.13, F, 5.60, Found: C, 77.41, 77.16, H, 7.74, N, 4.19 3.97, F, 5.78.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux temperature
  3. customquenched with an excess amount of ethyl acetate
  4. filtrationThe mixture was filtered through Celite
  5. dry with materialThe filtrate was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customColumn chromatography (ethyl acetate or CHCl3 ::MeOH::9:1) gave the product

Sources & evidence

ORD record
ord-de635c6913ed43cea0cd9a8fc549ac81
Source dataset
uspto-grants-1996_07
Patent number
US05532243

Reaction notes

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