Lithium Hydroxide → 3-(Tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylic acid

HRID 218065

반응식

HRID 218065 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:14]([CH2:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 68465572Methyl 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylate

생성물 1

HCID 684690633-(Tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylic acid수율 93.4%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of methyl 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylate (0.350 g, 1.31 mmol) in THF-methanol (6.0 mL, 1:1) was added a solution of lithium hydroxide (0.100 g in 1 mL of water, 3.94 mmol), and the reaction was stirred at ambient temperature for 3 h. The solvent was evaporated, the residue was acidified to pH 4 with 1 M aqueous hydrochloric acid, and extracted with ethyl acetate (50 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried (anhydrous sodium sulfate), and concentrated to obtain 0.31 g (92% yield) of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-oct-6-ene-7-carboxylic acid, as a white solid (1H NMR (CDCl3, 300 MHz): δ 6.76 (bs, 1H), 3.76-3.62 (m, 1H), 3.58-3.42 (m, 2H), 3.11-2.94 (m, 2H), 2.84-2.67 (m, 1H), 2.46-2.23 (m, 1H), 1.42 (s, 9H). MS (m/z): 254 (M+1), 198 (M+1-56)).

후처리

  1. customThe solvent was evaporated
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4911542411dc4b39862ba0f96a5cd79e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198296B2

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