Water → HCID 60064197, compound

HRID 412598Notes

Reaction equation

HRID 412598 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20](O)=[O:21])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.B.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH2:19][CH2:20][OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 60064121HCID 60064121, compound

Product 1

HCID 60064197HCID 60064197, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-4-ethoxycarbonyl-piperidin-4-ylacetic acid (2.34 g) in tetrahydrofuran (60 ml) was added a 1M borane tetrahydrofuran solution (7.42 ml) at −78° C., and the mixture was allowed to warm to room temperature in 15 hours in stirring. After completion of the reaction, water and potassium carbonate were added, and the mixture was stirred at room temperature for 1 hour. Water was added and the mixture was washed with hexane. The aqueous layer was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was dried under reduced pressure to give the title compound (1.92 g).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. washthe mixture was washed with hexane
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-e968f937d40043f7b08662cda1f50100
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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