Sodium Hydroxide → HCID 68473945, compound

HRID 2191122Notes

Reaction equation

HRID 2191122 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O.C(OCC)(=O)C>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][CH:5]([CH2:3][OH:2])[CH:6]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 68480332HCID 68480332, compound

Product 1

HCID 68473945HCID 68473945, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.5 g (4.2 mmol) (3SR,4SR)-3-(3,4-Difluoro-phenyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester and 0.16 g (4.2 mmol) LiAlH4 in 50 mL THF was stirred at room temperature for 1 h. Ethyl acetate, THF, water and NaOH aq. was added. Na2SO4 was added, the mixture was filtered off and evaporated to dryness. The residue was subjected to column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to afford after evaporation of the product containing fractions 1.06 g (77%) of the title compound as viscous colorless oil. MS (m/e): 228.1 [(M+H-Boc)+].

Workup

  1. filtrationthe mixture was filtered off
  2. customevaporated to dryness
  3. customformed from ethyl acetate and heptane
  4. customto afford
  5. customafter evaporation of the product
  6. additioncontaining fractions 1.06 g (77%) of the title compound as viscous colorless oil

Sources & evidence

ORD record
ord-7ab0944825524f30bd28d234c1f12783
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

Loading…