Water → Lurosetron

HRID 2081233Notes

Reaction equation

HRID 2081233 reaction equation
[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:19]=[CH:20][N:21](C(OCC5C=CC=CC=5)=O)[C:22]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.O.[OH-].[Na+]>C(O)C.Cl>[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:19]=[CH:20][NH:21][C:22]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15712526Phenylmethyl 4-[(6-fluoro-2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido [4,3-b]indol-2-yl)methyl]-5-methyl-1H-imidazole-1-carboxylate

Product 1

HCID 172999LurosetronYield 71.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of phenylmethyl 4-[(6-fluoro-2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido [4,3-b]indol-2-yl)methyl]-5-methyl-1H-imidazole-1-carboxylate (100 mg) in ethanol (20 ml) and 2N hydrochloric acid (10 ml) was heated on a steam bath for 10 min. The cooled reaction mixture was then added to water (5 ml) and 2N sodium hydroxide (20 ml), and extracted with ethyl acetate (2×75 ml). The combined, dried organic extracts were adsorbed onto silica and purified by FCC eluting with System A (100:8:1) to give a solid which was triturated with ether to give the title compound (50 mg), m.p. 232°-233°.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (2×75 ml)
  3. custompurified by FCC
  4. washeluting with System A (100:8:1)
  5. customto give a solid which
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-8b3f82d6375e4efe8d82c09e607c6716
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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