1,4-Dioxane hydrochloride → HCID 58423784, compound

HRID 1408806Notes

Reaction equation

HRID 1408806 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2([CH2:24][C:25]([O:27][CH3:28])=[O:26])[NH:17]S(C(C)(C)C)=O.Cl.O1CCOCC1>CO>[NH2:17][C:5]1([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:4]2[C:14](=[CH:15][CH:16]=[C:2]([Br:1])[CH:3]=2)[O:13][C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:6]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67384718HCID 67384718, compound

Product 1

HCID 58423784HCID 58423784, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(6-bromo-4-(1,1-dimethylethylsulfinamido)spiro[chroman-2,1′-cyclohexane]-4-yl)acetate (200 mg, 0.42 mmol) in MeOH (2 mL) was added 4 N HCl/1,4-dioxane (2 mL). After stirring for 30 minutes, the mixture was concentrated. The residue was dissolved in MeOH (1 mL) stirring for 5 minutes and evaporated again to afford methyl 2-(4-amino-6-bromospiro[chroman-2,1′-cyclohexane]-4-yl)acetate (140 mg, 90%). 1H NMR (CDCl3): 1.22-1.38 (m, 1H), 1.39-1.52 (m, 6H), 1.72-1.88 (m, 3H), 1.93-2.02 (d, 2H), 2.13-2.24 (t, 1H), 2.59 (d, 1H), 2.86 (d, 1H), 3.65 (s, 3H), 6.74 (d, 1H), 7.24 (s, 1H), 7.52 (s. 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in MeOH (1 mL)
  3. stirringstirring for 5 minutes
  4. customevaporated again

Sources & evidence

ORD record
ord-a5ec7c71d7e3459cb21d565c36c44cd0
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

Loading…