Water → Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylate

HRID 2366479Notes

Reaction equation

HRID 2366479 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.ClCCl>[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)=[CH:8][CH:7]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86613864Tert butyl 4-(4-(methoxy(methyl)carbamoyl)phenyl)piperidine-1-carboxylate

Product 1

HCID 11254770Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylateYield 27%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 88A (0.8 g, 2.3 mmol) in tetrahydrofuran (5 mL) was cooled to −78° C. and treated with lithium aluminum hydride (0.25 g, 6.6 mmol). The mixture was stirred for 30 minutes and treated with water (1 mL) and 15% sodium hydroxide (0.25 mL). Dichloromethane was added and the mixture dried over magnesium sulfate and filtered through silica gel. The solution was concentrated and purified by flash chromatography on silica gel using 1:1 hexane/ethyl acetate to provide the title compound (0.18 g).

Workup

  1. dry with materialthe mixture dried over magnesium sulfate
  2. filtrationfiltered through silica gel
  3. concentrationThe solution was concentrated
  4. custompurified by flash chromatography on silica gel using 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-0099c68ad03942ffbe6e7e8c54579c00
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

Loading…