Ammonium Chloride → tert-butyl (3S,4S)-4-(4-amino-2-chlorophenoxy)-3-fluoropiperidine-1-carboxylate

HRID 633422ノート

反応式

HRID 633422 の反応式
[Cl:1][C:2]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C@@H:6]1[F:18].[NH4+].[Cl-]>CCO.O.CCOC(C)=O.[Fe]>[NH2:23][C:21]1[CH:20]=[CH:19][C:3]([O:4][C@H:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][C@@H:6]2[F:18])=[C:2]([Cl:1])[CH:22]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 86704516tert-butyl (3S,4S)-4-(2-chloro-4-nitrophenoxy)-3-fluoropiperidine-1-carboxylate

生成物 1

HCID 86704517tert-butyl (3S,4S)-4-(4-amino-2-chlorophenoxy)-3-fluoropiperidine-1-carboxylate収率 45%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 8857Ethyl Acetate溶媒HCID 19096565Water ethanol溶媒

反応条件

温度
90 °C

実験手順

A mixture of tert-butyl (3S,4S)-4-(2-chloro-4-nitrophenoxy)-3-fluoropiperidine-1-carboxylate (0.8 g, 1.0 eq, 2.2 mmol), Fe (0.6 g, 5.0 eq, 10.8 mmol) and NH4Cl (0.6 g, 5.0 eq, 10.8 mmol) in EtOH/H2O (1:1, 50 mL) was stirred at 90° C. for 1 hour. The mixture was cooled to room temperature and concentrated under reduced pressure to leave a crude solid. The crude mixture was dissolved in EtOAc (50 mL) and partitioned with H2O (50 mL). Organic layers were separated and the aqueous layer was washed with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to give the desired product in 45% yield. This product was taken to next step with out further purification.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customto leave a crude solid
  4. custompartitioned with H2O (50 mL)
  5. customOrganic layers were separated
  6. washthe aqueous layer was washed with EtOAc (50 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1902c28a453d4b70bd690f74c441e576
出典データセット
uspto-grants-2016_04
特許番号
US09321763B2

反応ノート

読み込み中…