Hydrochloric Acid → Trans-6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 539326Notes

Reaction equation

HRID 539326 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]1([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]1)[C:5]2=[N:18]S(C(C)(C)C)=O.Cl.CCOCC>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8]([CH2:7][C:6]3([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]3)[C:5]2=[NH:18])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67043683N-(5'-bromo-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

Product 1

HCID 67979447Trans-6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-(5′-bromo-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 19 Step 1, mixture of isomers, 2 g, 4.85 mmol) in anhydrous 1,4-dioxane (25 mL) was added 4M HCl in 1,4-dioxane (12.12 mL, 48.50 mmol). A white precipitate was formed immediately and the resulting cloudy mixture was stirred under a nitrogen atmosphere at r.t. for 90 min. Et2O (30 mL) was added and the solid was filtered off and washed with Et2O. The solid was partitioned between DCM (40 mL) and sat. aq. NaHCO3 (40 mL). The phases were separated and the organic layer concentrated. The crude title compound (1.41 g) was used directly in the next step. MS (EI) m/z 307 M+.

Workup

  1. customA white precipitate was formed immediately
  2. filtrationthe solid was filtered off
  3. washwashed with Et2O
  4. customThe solid was partitioned between DCM (40 mL) and sat. aq. NaHCO3 (40 mL)
  5. customThe phases were separated
  6. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-7305268eb5dd49458db2e5741ad52411
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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