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Sodium Hydroxide → (r)-1-(4-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid

HRID 413677
Notes
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Reaction equation

HRID 413677 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]#[C:14][CH2:15][N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH:27]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:16]([CH2:15][C:14]#[C:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:17]=2[CH:30]=[CH:29][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53904801(R)-1-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 69463379(r)-1-(4-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-2-butyn-1-yl)-3-piperidinecarboxylic acidYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (3.5 g, 8.7 mmol) was dissolved in ethanol (40 ml). 5 N Sodium hydroxide (4 ml) was added and the mixture was allowed to stand for 3 days. Ethanol was evaporated in vacuo and the residue was dissolved in water (50 ml). The solution was washed with diethyl ether (30 ml) and acetic acid (3 ml) was added to the aqueous phase which subsequently was extracted with dichloromethane (50 ml). The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The residue was filtered through silica gel (20 g) using ethanol as eluent. The solvent was evaporated and acetone was added to the residue. The solid was isolated by filtration and dried to give 1.8 g (55%) of the title compound.

Workup

  1. customEthanol was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water (50 ml)
  3. washThe solution was washed with diethyl ether (30 ml) and acetic acid (3 ml)
  4. additionwas added to the aqueous phase which
  5. extractionsubsequently was extracted with dichloromethane (50 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent was evaporated in vacuo
  8. filtrationThe residue was filtered through silica gel (20 g)
  9. customThe solvent was evaporated
  10. additionacetone was added to the residue
  11. customThe solid was isolated by filtration
  12. customdried

Sources & evidence

ORD record
ord-6622dfed51e14d488f27741d88a9b54f
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06569849B1

Reaction notes

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