Sodium Hydroxide → HCID 57964712, compound

HRID 2403532Notes

Reaction equation

HRID 2403532 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28](O)=[O:29])[CH:23]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][OH:29])[CH:23]=3)[CH2:20][CH2:21]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57964332HCID 57964332, compound

Product 1

HCID 57964712HCID 57964712, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.5 g (3.59 mmol) of 4-{2-[4-(3-carboxyphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester in 20 mL of dry tetrahydrofuran is cooled to −10° C. under argon. An addition of 11 mL of a 1M solution of boranetetrahydrofuran complex in tetrahydrofuran is performed at −10° C. Stirring is maintained overnight at room temperature. The mixture is cooled to 0° C. and 12 mL of 1N aqueous sodium hydroxide solution are added. The product is extracted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is stirred with diisopropyl ether, filtered and dried under reduced pressure to give 1.0 g (69%) of 4-{2-[4-(3-hydroxymethylphenyl)piperazin-1-yl]ethyl}piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customis performed at −10° C
  2. temperatureThe mixture is cooled to 0° C.
  3. extractionThe product is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. stirringThe residue is stirred with diisopropyl ether
  9. filtrationfiltered
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-03e35b36cdb048d8a07cd4cc237c1be3
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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