1,4-Dioxane → HCID 89649349, compound

HRID 2207674Notes

Reaction equation

HRID 2207674 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:35])=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C@H:16]3[CH2:20][CH2:19][C@:18]4([CH2:24][CH2:23][N:22]([CH3:25])[C:21]4=[O:26])[N:17]3C(OC(C)(C)C)=O)[C:11]=2[CH3:34])[CH:9]=1)[CH3:2].O1CCOCC1>Cl>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:35])=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C@H:16]3[CH2:20][CH2:19][C@:18]4([CH2:24][CH2:23][N:22]([CH3:25])[C:21]4=[O:26])[NH:17]3)[C:11]=2[CH3:34])[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 131735926HCID 131735926, compound

Product 1

HCID 89649349HCID 89649349, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl (2R,5R)-2-[4-(5-ethoxy-2-fluoro-phenyl)-3-methyl-2-pyridyl]-7-methyl-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (which may be prepared as described in Description 100)(74.2 mg, 0.1500 mmol) in 4M HCl in dioxane (0.38 mL, 1.53 mmol) was stirred for 2 hours. The reaction was then concentrated in vacuo. The residue was loaded onto an SCX cartridge which was eluted with MeOH and 0.5 M methanolic ammonia. The basic fractions were combined and concentrated in vacuo to give (2R,5R)-2-[4-(5-ethoxy-2-fluoro-phenyl)-3-methyl-2-pyridyl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one (55.6 mg, 0.1450 mmol, 94.524% yield) as a colourless oil (5182RTS331-A1, >95% pure);

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. washwas eluted with MeOH and 0.5 M methanolic ammonia
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c76fe9359d842d1b1807346344571db
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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