4-Nitrobenzoic Acid → Benzyl trans-3-fluoro-4-[(4-nitrobenzyl)oxy]piperidine-1-carboxylate

HRID 1926648노트

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HRID 1926648 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[F:34][C@H:35]1[C@@H:40]([OH:41])[CH2:39][CH2:38][N:37]([C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[CH2:36]1.[N+:52]([C:55]1[CH:63]=[CH:62][C:58]([C:59](O)=O)=[CH:57][CH:56]=1)([O-:54])=[O:53]>C1COCC1>[F:34][C@H:35]1[C@H:40]([O:41][CH2:59][C:58]2[CH:62]=[CH:63][C:55]([N+:52]([O-:54])=[O:53])=[CH:56][CH:57]=2)[CH2:39][CH2:38][N:37]([C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[CH2:36]1

참가 물질

6

반응물 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 52324487(3R,4S)-Benzyl 3-fluoro-4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 68668648Benzyl trans-3-fluoro-4-[(4-nitrobenzyl)oxy]piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of triphenylphosphine (120.1 g, 0.458 mol) in THF (2 L) was added DIAD (92.6 g, 0.458 mol) with stirring under nitrogen at 0° C. The resulting suspension was stirred for 40 min, and then a solution of benzyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate (58 g, 0.229 mol) and 4-nitrobenzoic acid (45.9 g, 0.275 mol) in THF was added slowly over 1.5 h. The resulting orange solution was allowed to warm to room temperature and stirred for 48 h. The mixture was concentrated under reduced pressure to a crude oil was purified by column chromatography (EtOAc:petroleum ether=1:40) to afford benzyl trans-3-fluoro-4-[(4-nitrobenzyl)oxy]piperidine-1-carboxylate as an off-white solid.

후처리

  1. stirringThe resulting suspension was stirred for 40 min
  2. temperatureto warm to room temperature
  3. stirringstirred for 48 h
  4. concentrationThe mixture was concentrated under reduced pressure to a crude oil
  5. customwas purified by column chromatography (EtOAc:petroleum ether=1:40)

출처 및 근거

ORD 기록
ord-0f417f513be748a59111fec991e35afa
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183245B2

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