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Ethyl Acetate → Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 336627
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인쇄 미리보기

반응식

HRID 336627 반응식
[O:1]1[CH2:3][C:2]21[CH2:9][CH:8]1[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:5]([CH2:6][CH2:7]1)[CH2:4]2.C([O-])(O)=O.[Na+].C(OCC)(=O)C>O1CCCC1>[CH:3]([CH:2]1[CH2:4][CH:5]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH:8]([CH2:7][CH2:6]2)[CH2:9]1)=[O:1]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 74394144Benzyl 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane]-8-carboxylate

생성물 1

HCID 51030438Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
4 °C

실험 절차

To a cold (0° C.) solution of EXAMPLE 84A (3.5 g) in tetrahydrofuran (40 mL) was added boron trifluoride diethyl ether complex (0.82 mL). The mixture was stirred at 3-5° C. for 3 hours. Aqueous saturated NaHCO3 was added, followed by ethyl acetate (200 mL). The organic layer was separated, washed with water (twice) and concentrated to dryness. Toluene was added and the mixture was concentrated under vacuum to provide the title compound.

후처리

  1. customThe organic layer was separated
  2. washwashed with water (twice) and
  3. concentrationconcentrated to dryness
  4. additionToluene was added
  5. concentrationthe mixture was concentrated under vacuum

출처 및 근거

ORD 기록
ord-19222742187240558bbb5ec36574dc5c
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889675B2

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