Sodium Hydroxide → 2-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid

HRID 1018301Notes

Reaction equation

HRID 1018301 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:7]=1[CH2:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:5])C.[OH-].[Na+]>C(O)C>[C:18]12([CH2:17][C:7]3[NH:8][C:9]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[CH:10][C:6]=3[C:4]([OH:5])=[O:3])[CH2:25][CH:24]3[CH2:23][CH:22]([CH2:21][CH:20]([CH2:26]3)[CH2:19]1)[CH2:27]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117175262-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 113820842-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product of step b (750 mg, 2.06 mmol) in ethanol (45 ml) was added sodium hydroxide (5 ml of 6.0M solution). The mixture was heated at reflux for 48 h, it was allowed to cool to room temperature and concentrated to small volume under reduced pressure. The concentrated solution was diluted with 2M hydrochloric acid (40 ml), the precipitated solid was filtered, washed with water and dried to afford the acid (660 mg, 94%). 1H NMR (300 MHz, CDCl3) 11.5 (1H, br s), 8.26 (1H, br s), 7.48 (2H, m), 7.40 (2H, m), 7.26 (1H, m), 6.94 (1H, d), 2.87 92H, s), 1.97 (3H, br s), 1.63 (12H, m).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 h
  3. concentrationconcentrated to small volume under reduced pressure
  4. additionThe concentrated solution was diluted with 2M hydrochloric acid (40 ml)
  5. filtrationthe precipitated solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-721e89b93ae94c7b9ac7220275d5d532
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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