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

HRID 520331노트

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HRID 520331 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
15 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-63dda7ce40584841905cdf810e586913
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326985B2

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