Lithium hydroxide, monohydrate → 2-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

HRID 712803ノート

反応式

HRID 712803 の反応式
[CH:1]12[CH2:6][CH:5]1[CH2:4][C@H:3]([C:7]([O:9]CC)=[O:8])[N:2]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].O[Li].O>O1CCOCC1.O>[C:15]([O:14][C:12]([N:2]1[CH:3]([C:7]([OH:9])=[O:8])[CH2:4][CH:5]2[CH:1]1[CH2:6]2)=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 58405350(3R)-2-tert-butyl 3-ethyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

生成物 1

HCID 213390052-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of (3R)-2-tert-butyl 3-ethyl 2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate (D26) (diastereoisomer mixture) (3.4 g, 13.3 mmol) in dioxane (15 ml) and water (15 ml), LiOH H2O (2.2 g, 53 mmol). The mixture was stirret at RT for 18 h. Dioxane was evaporated off and water was washed with Et2O (2×40 ml) then the pH was adjusted to ˜4 by addition of citric acid and the resulting aqueous phase was extacted with DCM (200 ml), washed with water (20 ml), dried over Na2SO4 and evaporated in vacuo to afford the title compound (D27) (2.75 g) as diastereoisomer mixture with syn-anti ratio 10/2.

後処理

  1. customDioxane was evaporated off
  2. washwater was washed with Et2O (2×40 ml)
  3. additionthe pH was adjusted to ˜4 by addition of citric acid
  4. washwashed with water (20 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-4408db64c5b346ab9b81bdc033596f28
出典データセット
uspto-grants-2015_11
特許番号
US09181279B2

反応ノート

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