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

HRID 539326

반응식

HRID 539326 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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+.

후처리

  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

출처 및 근거

ORD 기록
ord-7305268eb5dd49458db2e5741ad52411
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865911B2

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