Water → (r)-1-(3-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-2-hydroxypropyl)-3-piperidinecarboxylic acid

HRID 413683Notes

Reaction equation

HRID 413683 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH:13]([OH:30])[CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].O>C(O)C>[CH:26]1[C:17]2[CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:15]([CH2:14][CH:13]([OH:30])[CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:16]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70010011(R)-1-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-hydroxy-propyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 70010077(r)-1-(3-(10,11-Dihydro-5h-dibenzo[b,f]azepin-5-yl)-2-hydroxypropyl)-3-piperidinecarboxylic acidYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.38 g, 0.93 mmol) was dissolved in ethanol (5 ml), 2 N sodium hydroxide (1.54 ml, 3.07 mmol) was added and the homogeneous mixture was stirred at room temperature for 24 h. Water (15 ml) was added and the ethanol was removed in vacuo. The aqueous solution was washed with ether (2×10 ml) and pH was adjusted to 6 by addition of 1N hydrochloric acid. The acidic mixture was extracted with dichloromethane (2×15 ml). The combined organic extracts were washed with water (20 ml), dried (MgSO4) and concentrated in vacuo. The residue was triturated with ether and the product collected by filtration to give 0.23 g (66%) of the title compound as a powder.

Workup

  1. customthe ethanol was removed in vacuo
  2. washThe aqueous solution was washed with ether (2×10 ml) and pH
  3. additionwas adjusted to 6 by addition of 1N hydrochloric acid
  4. extractionThe acidic mixture was extracted with dichloromethane (2×15 ml)
  5. washThe combined organic extracts were washed with water (20 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether
  9. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-fcf83fa0892345f1b8ddb87230919e68
Source dataset
uspto-grants-2003_05
Patent number
US06569849B1

Reaction notes

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