Tetrahydrofuran → HCID 44252684, compound

HRID 76940Notes

Reaction equation

HRID 76940 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7][C:6]([N:15]([CH3:21])[C:16](=O)[CH2:17][CH2:18][CH3:19])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[CH2:16]([N:15]([CH3:21])[C:6]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4][C:3]([N:2]([CH3:28])[CH3:1])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7]1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 68632404N-(4-dimethylamino-1,4-diphenyl-cyclohexyl)-N-methyl-butyramide

Product 1

HCID 44252684HCID 44252684, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound from step 1 (200 mg, 0.528 mmol) was dissolved in abs. THF (15 mL). LiAlH4 (39 mg, 1.06 mmol) was added in argon. The batch was boiled for 7 h with reflux. The batch was then cooled to room temperature, mixed with THF (12 mL) and H2O (5 mL) with ice cooling and subsequently stirred for 30 min. The batch was filtered over a fritted glass filter with diatomaceous earth and subsequently rinsed with dichloromethane (50 mL). The combined filtrates were concentrated to low volume in a vacuum.

Workup

  1. temperaturewith reflux
  2. filtrationThe batch was filtered over a fritted glass
  3. filtrationfilter with diatomaceous earth
  4. washsubsequently rinsed with dichloromethane (50 mL)
  5. concentrationThe combined filtrates were concentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-ff3c2e5d72f34e7d8c9fe3e4253e8efa
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

Loading…