Aluminium lithium hydride → tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

HRID 2168096Notes

Reaction equation

HRID 2168096 reaction equation
[F:1][C:2]1([C:15](OCC)=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1([CH2:15][OH:16])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21306965Ethyl N-Boc-4-fluoropiperidine-4-carboxylate

Product 1

HCID 22248400tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Tert-butyl 4-ethyl 4-fluoropiperidine-1,4-dicarboxylate (2 g) was taken up in tetrahydrofuran (20 ml) and cooled in an ice bath. Lithium aluminum hydride (1.0M in dioxane, 5.09 mL) was added dropwise. The reaction was stirred at room temperature for 2 hours. The reaction was quenched with water and with 1M aqueous NaOH solution and then stirred another 1 hour at room temperature. The mixture was extracted with ethyl acetate, and the extracts were combined and washed with water and with brine, dried over MgSO4, filtered and concentrated under vacuum. The crude product was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with water and with 1M aqueous NaOH solution
  3. stirringstirred another 1 hour at room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water and with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-fc3548cb7a464dc994970aa7a2d996ba
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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