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

HRID 1041993ノート

反応式

HRID 1041993 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 86708534(3R,4S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-fluoropiperidine-1-carboxylate

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-7566bb91d60a485580b28aa36a47d131
出典データセット
uspto-grants-2013_10
特許番号
US08557809B2

反応ノート

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