Aluminium lithium hydride → HCID 90219228, compound

HRID 1486157Notes

Reaction equation

HRID 1486157 reaction equation
[CH2:1]([N:8]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:9]([C@H:11]1[C@H:16]([C:17](=O)[N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14][C@@H:13]([CH2:34][C:35](OC)=[O:36])[CH2:12]1)=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:8]([CH2:9][C@H:11]1[C@H:16]([CH2:17][N:18]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:15][CH2:14][C@@H:13]([CH2:34][CH2:35][OH:36])[CH2:12]1)[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131732178HCID 131732178, compound

Product 1

HCID 90219228HCID 90219228, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a cooled (−10° C.) solution of (racemic)-Methyl 2-[(1R,3R,4R)-3,4-bis(dibenzylcarbamoyl)cyclohexyl]acetate (8.18 g, 13.5 mmol) in THF (40 mL) is added, drop wise, lithium aluminum hydride (50 mL, 1M in THF). On complete addition, the cold bath is removed and stirring continued for 15 min. The resulting solution is heated to 55° C. and stirred at this temperature for 2.5 hr. This solution is cooled to 0° C. To the resulting solution is added, drop wise, water (1.9 mL) then NaOH (1.9 mL, 5M aqueous) then water (0.95 mL). The resulting mixture is diluted with Et2O (100 mL), filtered through Celite and the filtrate concentrated under vacuum to give the title compound as an oil (8.1 g). ESI-MS (m/z) 547 (MH)+.

Workup

  1. additionis added
  2. additionOn complete addition
  3. customthe cold bath is removed
  4. stirringstirred at this temperature for 2.5 hr
  5. temperatureThis solution is cooled to 0° C
  6. additionTo the resulting solution is added
  7. additionThe resulting mixture is diluted with Et2O (100 mL)
  8. filtrationfiltered through Celite
  9. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-e439077028d74159bd4e131e00f2e5f3
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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