Ammonium formate → (S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

HRID 1520763ノート

反応式

HRID 1520763 の反応式
C1(C(=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[O:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 86654632(S)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate

生成物 1

HCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate収率 94.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

A suspension of (S)-tert-butyl 2-(4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate (54.1 g, 122 mmol), ammonium formate (116 g, 1.83 mol) and Pd/C 5% (6.5 g, 3.06 mmol) in methanol (930 ml) was stirred at 60° C. for 2 h. The reaction mixture was filtered and concentrated. The residue was dissolved in ethyl acetate and water. The organic phase was extracted twice with 0.5M HCl. The combined aqueous phases were basified with 2M-NaOH and extracted twice with DCM. The organic phases were dried over magnesium sulfate, filtered and dried in vacuo, to yield 31.95 g off-white solid. MS (ISP): 279.1 ([M+H]+).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionThe organic phase was extracted twice with 0.5M HCl
  5. extractionextracted twice with DCM
  6. dry with materialThe organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-1fbe18ed13bf4d389a72d5ab2a4a8bad
出典データセット
uspto-grants-2015_07
特許番号
US09073911B2

反応ノート

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