Sodium Bicarbonate → HCID 21408253, compound

HRID 2072503Notes

Reaction equation

HRID 2072503 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=5)[C@H:19]4O)[CH2:13][CH2:12]3)[C:10](=[O:31])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.CCOCC>[CH3:29][O:28][C:22]1[CH:21]=[C:20]2[C:25]([CH2:26][CH2:27][C:18]([CH2:17][N:14]3[CH2:15][CH2:16][C:11]4([N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH2:8][NH:9][C:10]4=[O:31])[CH2:12][CH2:13]3)=[CH:19]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23350293Acetic acid sulfuric acidHCID 53770694HCID 53770694, compound

Product 1

HCID 21408253HCID 21408253, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

trans-1-Phenyl-8-[(1,2,3,4-tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl)methyl]-1,3,8-traizaspiro[4.5]decan-4-one (5.0 g, see example 196) is added in portions to 25 ml of 20% v/v sulfuric acid/acetic acid. The resulting mixture is stirred for 16 hours at room temperature protected from moisture by a drying tube. The reaction mixture is warmed on a steam bath for 5 minutes, cooled, poured onto ice, basified with solid sodium bicarbonate, and extracted with methylene chloride. The dried methylene chloride solution is concentrated to give a crude solid. Trituration with 1:1 absolute ethanol/ether yields 3.0 g of the title compound, melting point 184°-186° C.

Workup

  1. customprotected from moisture by a drying tube
  2. temperatureThe reaction mixture is warmed on a steam bath for 5 minutes
  3. temperaturecooled
  4. additionpoured onto ice
  5. extractionextracted with methylene chloride
  6. concentrationThe dried methylene chloride solution is concentrated
  7. customto give a crude solid

Sources & evidence

ORD record
ord-161f0a65f6fc4e61874dfec5db2a52b1
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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