Aluminium lithium hydride → HCID 118382885, compound

HRID 2202763Notes

Reaction equation

HRID 2202763 reaction equation
[CH:1]1([C@H:7]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:9]([C:19](=[O:24])N(OC)C)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]1([C@H:7]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C@H:9]([CH:19]=[O:24])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118383643HCID 118383643, compound

Product 1

HCID 118382885HCID 118382885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2S,4S)-tert-butyl 4-cyclohexyl-2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (1.14 g, 3.35 mmol) was treated with THF (20 mL), cooled to 0° C. in an ice bath and then treated with lithium aluminum hydride (1.0M solution in THF, 3.35 mL, 3.35 mmol) slowly dropwise over 3 min. The solution was then stirred at 0° C. for 45 min. The reaction mixture was quenched with a solution of sodium potassium tartrate, stirred at room temperature for 20 min, then extracted with EtOAc (3×50 mL), washed with brine and dried over MgSO4, filtered and concentrated affording crude (2S,4S)-tert-butyl 4-cyclohexyl-2-formylpyrrolidine-1-carboxylate as a clear, viscous oil. MS (ESI) 304.1 [M+Na]. The crude material was used in the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with a solution of sodium potassium tartrate
  2. stirringstirred at room temperature for 20 min
  3. extractionextracted with EtOAc (3×50 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-651ed3bb5fd04f1f8fa1de61fcc12383
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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