N-methylhydroxylamine hydrochloride → Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate

HRID 1503450Notes

Reaction equation

HRID 1503450 reaction equation
CN[OH:3].Cl.C[O-].[Na+].[Br:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14]3([CH2:34][CH2:33][CH:32]([O:35][CH3:36])[CH2:31][CH2:30]3)[C:15]2([NH:23][S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])[C:18]([O:20][CH2:21][CH3:22])=C)=[CH:11][CH:10]=1>CO>[Br:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C:14]3([CH2:34][CH2:33][CH:32]([O:35][CH3:36])[CH2:31][CH2:30]3)[C:15]2([NH:23][S:24]([C:26]([CH3:28])([CH3:29])[CH3:27])=[O:25])[C:18]([O:20][CH2:21][CH3:22])=[O:3])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 58198087N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 58197767Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of MeNHOH.HCl (24.4 mg, 0.29 mmol) in MeOH (5 mL) was added NaOMe (10 wt % in MeOH, 141 mg, 0.26 mmol) and the mixture was stirred for 5 min. Then to a solution of compound 5 (104 mg, 0.29 mmol) in MeOH (8 mL) was added to above solution. Then final reaction mixture was stirred at room temperature for 45 min. Then the solution was concentrated and the residue was purified, which was purified preparative TLC to give compound 6 (80 mg, 68%) as a white solid.

Workup

  1. customThen final reaction mixture
  2. stirringwas stirred at room temperature for 45 min
  3. concentrationThen the solution was concentrated
  4. customthe residue was purified
  5. customwhich was purified preparative TLC

Sources & evidence

ORD record
ord-7599e86e7ed94a499799d3554dec4533
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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