Triethylamine → 2,2,2-Trifluoro-1-(9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

HRID 471067노트

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HRID 471067 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][OH:12])[CH:6]=[C:7]([F:9])[CH:8]=1.FC(F)(F)C(O)=O.[F:20][C:21]([F:36])([F:35])[C:22]([N:24]1[CH2:29][C:28]2([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[O:27][CH2:26][CH2:25]1)=[O:23].C(N(CC)CC)C>C(#N)C>[F:36][C:21]([F:20])([F:35])[C:22]([N:24]1[CH2:29][C:28]2([CH2:34][CH2:33][N:32]([CH2:2][C:3]3[CH:4]=[C:5]([CH2:10][CH2:11][OH:12])[CH:6]=[C:7]([F:9])[CH:8]=3)[CH2:31][CH2:30]2)[O:27][CH2:26][CH2:25]1)=[O:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 579893452-(3-(Bromomethyl)-5-fluorophenyl)ethanolHCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

생성물 1

HCID 579893802,2,2-Trifluoro-1-(9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
20 °C

실험 절차

A solution of 2-(3-(bromomethyl)-5-fluorophenyl)ethanol (example 41, step b) (3.6 g) and 2,2,2-trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate (example 12, step d) (5.66 g) in acetonitrile (80 mL) was treated with triethylamine (5.38 mL) and the mixture stirred at 20° C. for 20 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 2.5% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 4.9 g.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-dc5d9a6b5a3c442bada883255e855e41
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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