Aluminium lithium hydride → tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 733109Notes

Reaction equation

HRID 733109 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1([OH:22])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)#[N:8]>C1COCC1>[NH2:8][CH2:7][C:9]1([OH:22])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53399262tert-Butyl 4-cyano-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylateYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (84 mg, 2.2 mmol) in THF (5 mL), a solution of tert-butyl 4-cyano-4-hydroxypiperidine-1-carboxylate (200 mg, 0.88 mmol, step 1 of Example 22) in THF (1 mL) was added dropwise at 0° C. The mixture was stirred for 1 h at that temperature and Na2SO4.10H2O (400 mg) was added slowly, and the mixture was stirred for 5 h at room temperature. The mixture was filtered though a pad of Celite, washed with CH2Cl2 (20 mL×2), the filtrate was concentrated to give clear colorless oil. The residue was chromatographed on a column of silica gel eluting with CH2Cl2/MeOH/NH4OH (14:1:0.1) to give 120 mg (59%) of the title compound as white solid.

Workup

  1. additionwas added slowly
  2. filtrationThe mixture was filtered though a pad of Celite
  3. washwashed with CH2Cl2 (20 mL×2)
  4. concentrationthe filtrate was concentrated
  5. customto give clear colorless oil
  6. customThe residue was chromatographed on a column of silica gel eluting with CH2Cl2/MeOH/NH4OH (14:1:0.1)

Sources & evidence

ORD record
ord-7dd47319446b42a9bd74252c1da8e942
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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