Sodium Hydroxide → (S)-(1-Benzyl-3-methylpiperidin-3-yl)methanol

HRID 2366026Notes

Reaction equation

HRID 2366026 reaction equation
C([O:3][C:4]([C@@:6]1([CH3:19])[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@@:6]([CH2:4][OH:3])([CH3:19])[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66727374(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester

Product 1

HCID 66727443(S)-(1-Benzyl-3-methylpiperidin-3-yl)methanolYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester (1.64 g, 6.3 mmol) in dry THF (20 ml) was slowly added to a stirred suspension of LiAlH4 (0.71 g, 18.8 mmol) in dry THF (20 ml) under nitrogen atmosphere. After the addition the mixture was refluxed for 1.5 h. The solution was cooled with an ice bath, stirred vigorously and 2.5 M NaOH was added carefully drop by drop until no reaction occurred and a white precipitate was formed. The solvent was decanted and the solid washed with EtOAc (2×20 ml). The combined organic phases were dried, filtered and evaporated to dryness to give 1.29 g of the alcohol product as a white powder.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas refluxed for 1.5 h
  3. temperatureThe solution was cooled with an ice bath
  4. customa white precipitate was formed
  5. customThe solvent was decanted
  6. washthe solid washed with EtOAc (2×20 ml)
  7. customThe combined organic phases were dried
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-6486a6511eab446f8b980ac23e652261
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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