Sodium Hydroxide → 6-(tert-Butoxycarbonyl)-6-azaspiro[2.5]octane-1-carboxylic acid

HRID 520331ノート

反応式

HRID 520331 の反応式
[CH:1]1([C:16]([O:18]CC)=[O:17])[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.[OH-].[Na+]>C(O)C.O>[C:12]([O:11][C:9]([N:6]1[CH2:5][CH2:4][C:3]2([CH:1]([C:16]([OH:18])=[O:17])[CH2:2]2)[CH2:8][CH2:7]1)=[O:10])([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 497574526-(1,1-Dimethylethyl) 1-ethyl 6-azaspiro[2.5]octane-1,6-dicarboxylate

生成物 1

HCID 438107996-(tert-Butoxycarbonyl)-6-azaspiro[2.5]octane-1-carboxylic acid収率 86.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
15 °C

実験手順

To the solution of 165c (500 mg, 1.76 mmol) in ethanol (8 mL) was added sodium hydroxide (212 mg, 5.3 mmol) in water (4 mL). See FIG. 6. The mixture was stirred at 15° C. for 12 h. The solvent was evaporated under reduced pressure. The aqueous solution was acidified with dilute hydrochloride acid (0.5 M) slowly under ice bath until pH˜4, and extracted with EtOAc (10 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to give 6-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-1-carboxylic acid 165d (390 mg, 83%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 3.52-3.42 (m, 3H), 3.38-3.35 (m, 1H), 1.75-1.72 (m, 2H), 1.58-1.56 (m, 1H), 1.46-1.43 (m, 11H), 1.23-1.21 (m, 1H), 1.02-1.01 (m, 1H).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customThe aqueous solution was acidified with dilute hydrochloride acid (0.5 M) slowly under ice bath until pH˜4
  3. extractionextracted with EtOAc (10 mL×3)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-63dda7ce40584841905cdf810e586913
出典データセット
uspto-grants-2016_05
特許番号
US09326985B2

反応ノート

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