Phthalimide → (+/-)-Benzyl 3-(1,3-dioxoisoindolin-2-yl)-4-fluoropiperidine-1-carboxylate

HRID 69894ノート

反応式

HRID 69894 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[F:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[CH2:35][CH:34]1O.[C:50]1(=[O:60])[NH:54][C:53](=[O:55])[C:52]2=[CH:56][CH:57]=[CH:58][CH:59]=[C:51]12>C1(C)C=CC=CC=1>[O:55]=[C:53]1[C:52]2[C:51](=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:50](=[O:60])[N:54]1[CH:34]1[CH:33]([F:32])[CH2:38][CH2:37][N:36]([C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[CH2:35]1

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 42609255Benzyl 4-fluoro-3-hydroxypiperidine-1-carboxylate

生成物 1

HCID 86669189(+/-)-Benzyl 3-(1,3-dioxoisoindolin-2-yl)-4-fluoropiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of triphenylphosphine (3.0 equiv.) in toluene (0.25 M solution) was added DEAD (3.0 equiv.) at room temperature, which was stirred for 15 min. Then, (+/−)-benzyl 4-fluoro-3-hydroxypiperidine-1-carboxylate (1.0 equiv.) was added to the reaction mixture. After being stirred for 10 min, phthalimide (3.0 equiv.) was added and the reaction mixture was stirred for 15 h. The reaction mixture was extracted with ethyl acetate, which was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and filtered. After volatile materials were removed, (+/−)-benzyl 3-(1,3-dioxoisoindolin-2-yl)-4-fluoropiperidine-1-carboxylate was obtained by silica column chromatography (10% to 20% EtOAc in hexanes, 20%). LCMS (m/z): 383.0 (MH+), Rt=1.0 min.

後処理

  1. stirringAfter being stirred for 10 min
  2. stirringthe reaction mixture was stirred for 15 h
  3. extractionThe reaction mixture was extracted with ethyl acetate, which
  4. washwas washed with water and brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customAfter volatile materials were removed

出典と根拠

ORDレコード
ord-94ad96816b4846179ea1308b26866ee1
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

反応ノート

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