Diethyl Ether → 5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-imine

HRID 1965113

反応式

HRID 1965113 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:8]3([CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]3)[C:7](=[N:17]S(C(C)(C)C)=O)[C:6]=2[CH:24]=1.CCOCC>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:8]3([CH2:9][CH2:10][CH:11]([O:14][CH3:15])[CH2:12][CH2:13]3)[C:7](=[NH:17])[C:6]=2[CH:24]=1

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 67979520N-(5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide

生成物 1

HCID 679795445-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-imine収率 91.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of N-(5-bromo-4′-methoxy-3H-spiro[benzofuran-2,1′-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide (Example 29 Step 1, 2 g, 4.83 mmol) in anhydrous 1,4-dioxane (40 mL) was added 4M HCl in1,4-dioxane (12.07 mL, 48.27 mmol) and the resulting mixture was stirred under a nitrogen atmosphere at rt overnight. Et2O (30 mL) was added and the precipitate was filtered off and washed with Et2O, then partitioned between DCM (40 mL) and sat. aq. NaHCO3 (40 mL). The phases were separated and the organic layer concentrated, yielding 1.37 g of the crude title compound which was used immediately in the next step: MS (EI) m/z 309 M+.

後処理

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

出典と根拠

ORDレコード
ord-7d84b6c66945437b95d75d50151658ec
出典データセット
uspto-grants-2013_04
特許番号
US08415483B2

関連ノート

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