Trifluoroacetic acid → benzyl N-[(3R,4S)-3-fluoropiperidin-4-yl]carbamate

HRID 339706

反応式

HRID 339706 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]1[F:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C@H:13]1[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16][NH:15][CH2:14]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86708534HCID 86708534、化合物

生成物 1

HCID 68566554benzyl N-[(3R,4S)-3-fluoropiperidin-4-yl]carbamate収率 79.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(cis)-tert-Butyl 4-(benzyloxycarbonylamino)-3-fluoropiperidine-1-carboxylate (7.5 g, 21.3 mmol) was weighed into a 500 mL 1 neck round bottom and dissolved in 200 mL of DCM, followed by addition of TFA (16.4 mL, 213 mmol) and stirring at ambient temperature for 1 hour, at which time all bubbling had ceased and the reaction appeared complete by TLC. The crude reaction was concentrated in vacuo, followed by aqueous work-up with 2 N NaOH and DCM. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to afford benzyl(cis)-3-fluoropiperidin-4-ylcarbamate (4.25 g, 16.8 mmol, 79.2% yield) as a white solid.

後処理

  1. customThe crude reaction
  2. concentrationwas concentrated in vacuo
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-98909412d28e4f92a1b3ae15ba9a7b97
出典データセット
uspto-grants-2014_11
特許番号
US08895550B2

関連ノート

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