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

HRID 2401116ノート

反応式

HRID 2401116 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-d14f1fb0bed9481c937e7e3e4a1e30a9
出典データセット
uspto-grants-2014_08
特許番号
US08796278B2

反応ノート

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