Potassium tert-butoxide → 2-(5-Bromo-pyridin-2-yl)-8-oxa-2-aza-spiro[4.5]decan-1-one

HRID 2401116노트

반응식

HRID 2401116 반응식
C[O:2][C:3]([C:5]1([CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[CH2:12][CH2:11][C:5]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[C:3]2=[O:2])=[N:15][CH:16]=1

참가 물질

5

반응물 2

HCID 23665647Potassium tert-butoxideHCID 674786784-[2-(5-Bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester

생성물 1

HCID 674786592-(5-Bromo-pyridin-2-yl)-8-oxa-2-aza-spiro[4.5]decan-1-one수율 46%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[2-(5-bromo-pyridin-2-ylamino)-ethyl]-tetrahydro-pyran-4-carboxylic acid methyl ester in THF (15 mL) was added a solution of potassium t-butoxide (1 M in THF) (3.5 eq), and allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (15 mL), quenched with brine (2 mL). The aqueous layer was extracted with ethyl acetate (2×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. Purification over silica gel eluting with methanol in dichloromethane (0-10%) afforded 0.4 g (46%) of title compound.

후처리

  1. customquenched with brine (2 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customPurification over silica gel eluting with methanol in dichloromethane (0-10%)

출처 및 근거

ORD 기록
ord-d14f1fb0bed9481c937e7e3e4a1e30a9
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796278B2

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