Potassium tert-butoxide → 4-(7-Trifluoromethyl-benzo[d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2111733

반응식

HRID 2111733 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=2F)=[N:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 724345674-[(2-Fluoro-3-trifluoromethylphenyl)-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 588176024-(7-Trifluoromethyl-benzo[d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a room temperature mixture of 4-[(2-fluoro-3-trifluoromethyl-phenyl)-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.40 g, 3.59 mmol) in THF (20 mL) under nitrogen was added potassium tert-butoxide (3.60 mL of a 1M THF solution, 3.60 mmol) in one portion and the reaction heated at 60° C. for 1.5 h. After standing at room temperature overnight, the solvent was removed and the residue diluted with ethyl acetate (60 mL). The organics were washed with water (30 mL) and brine (30 mL) successively, dried over magnesium sulfate, filtered, and concentrated to give an amber solid. The crude product was chromatographed on silica using 40% ethyl acetate/heptane as eluent to afford 0.97 g (73%) of the desired product as a white solid, mp: 111-113° C.

후처리

  1. customthe solvent was removed
  2. additionthe residue diluted with ethyl acetate (60 mL)
  3. washThe organics were washed with water (30 mL) and brine (30 mL) successively
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an amber solid
  8. customThe crude product was chromatographed on silica using 40% ethyl acetate/heptane as eluent

출처 및 근거

ORD 기록
ord-42459509d7e6493098e6d203be48e45c
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521445B2

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