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

HRID 1926648ノート

反応式

HRID 1926648 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0f417f513be748a59111fec991e35afa
出典データセット
uspto-grants-2012_05
特許番号
US08183245B2

反応ノート

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