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Lithium Hydroxide → (R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid

HRID 77333
ノート
印刷プレビュー

反応式

HRID 77333 の反応式
C([O:3][C:4]([CH:6]1[C@H:13]2[CH2:14][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)[N:7]1[S:15]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])=[O:16])=[O:5])C.[OH-].[Li+]>O1CCCC1.O>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[S:15]([N:7]1[CH:6]([C:4]([OH:5])=[O:3])[C@H:13]2[CH2:14][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]2)(=[O:17])=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 67155158(R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester

生成物 1

HCID 67155306(R)-7-(Naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid収率 98%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of (R)-7-(naphthalene-2-sulfonyl)-7-aza-bicyclo[4.2.1]nonane-8-carboxylic acid ethyl ester (0.55 g, 1.42 mmol) in tetrahydrofuran (15 mL) is added a solution of lithium hydroxide (1.2 g, 28.6 mmol) in water (15 mL). The reaction is heated to 80° C. for 16 h, and the solvent is removed in vacuo. The residue is dissolved in water and washed with diethyl ether. The aqueous layer is then acidified with 6 N hydrochloric acid to pH less than 4 and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated to afford the title compound as a yellow solid (0.50 g, 98% yield). LCMS (m/z): 360.07 (M+1), 358.12 (M−1).

後処理

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in water
  3. washwashed with diethyl ether
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-7661e73c103b45fabeba0b561fa5084b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841291B2

反応ノート

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