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

HRID 1965091ノート

反応式

HRID 1965091 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

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+.

後処理

  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

出典と根拠

ORDレコード
ord-6381a5454aa448fc9cc96a1eff624cb8
出典データセット
uspto-grants-2013_04
特許番号
US08415483B2

反応ノート

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