Sodium Hydroxide → 4-(3-Hydroxymethyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1928587Notes

Reaction equation

HRID 1928587 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[N:17][C:16]([C:19](OCC)=[O:20])=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[N:17][C:16]([CH2:19][OH:20])=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 687480884-(3-Ethoxycarbonyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 577083924-(3-Hydroxymethyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(3-ethoxycarbonyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (from Step 1, 0.64 g, 2.06 mmol) in THF (10 mL) at 0° C. was added lithium aluminum hydride (0.078 g, 2.06 mmol). The solution was allowed to warm to room temperature and stirred for 4 hours. The solution was diluted with THF, cooled to 0° C., and 1 mL of water was added followed by 1 mL of 15% NaOH and 3 mL of water. The solution was allowed to warm to room temperature and stirred for 15 minutes. MgSO4 was then added and the solution was stirred an additional 15 minutes, filtered and concentrated in vacuo. The residue was purified by flash chromatograph on silica gel with MeOH and CH2Cl2 to afford the desired product. 1H NMR (CDCl3): δ 8.03 (1H, s), 4.79 (2H, d), 4.25 (3H, m), 2.95 (2H, m), 2.58 (1H, t), 2.19 (2H, m), 1.98 (2H, m), 1.43 (9H, s).

Workup

  1. temperaturecooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 15 minutes
  4. stirringthe solution was stirred an additional 15 minutes
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatograph on silica gel with MeOH and CH2Cl2

Sources & evidence

ORD record
ord-9179375ddadc428e9638887b0d834e22
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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