N-Iodosuccinimide → HCID 59135497, compound

HRID 1993987Notes

Reaction equation

HRID 1993987 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[O:24][CH2:23][C@@H:19]3[CH2:20][NH:21][CH2:22][C@H:18]3[C@@H:17]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1C(=O)N([I:42])C(=O)C1>FC(F)(F)C(O)=O>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[O:24][CH2:23][C@@H:19]3[CH2:20][NH:21][CH2:22][C@H:18]3[C@@H:17]2[C:25]2[CH:30]=[C:29]([I:42])[C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 11648859HCID 11648859, compound

Product 1

HCID 59135497HCID 59135497, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (3aS,6R,7R,7aR)-6-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-7-(4-fluoro-2-methylphenyl)octahydropyrano[3,4-c]pyrrole (55.8 mg, 0.12 mmol) and NIS (53 mg, 0.23 mmol) in 2 mL trifluoroacetic acid was stirred at rt for 40 min. Volatiles were removed. The crude was purified by reverse phase HPLC to afford the title compound.

Workup

  1. customVolatiles were removed
  2. customThe crude was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-876c9e6b27db4a6cb4612bb4e5cfc047
Source dataset
uspto-grants-2010_01
Patent number
US07652058B2

Reaction notes

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