Methanol → Ethyl 4-(4-amino-3-phenylbutanamido)benzoate

HRID 2422942ノート

反応式

HRID 2422942 の反応式
[N+:1]([CH2:4][CH:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1)=[O:8])([O-])=O.CO>>[NH2:1][CH2:4][CH:5]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:6][C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1)=[O:8]

参加物

3

反応物 2

HCID 887MethanolHCID 67242330Ethyl 4-(4-nitro-3-phenyl-butyrylamino)benzoate

生成物 1

HCID 67243563Ethyl 4-(4-amino-3-phenylbutanamido)benzoate

実験手順

Ref. J. Org. Chem., 2000, 65, 8001. To a stirred solution of nitro compound 47 (0.749 g, 2.10 mmol) and NiCl2.6H2O (1.99 g, 8.40 mmol) in methanol (10 ml) NaBH4 (0.719 g, 18.93 mmol) was added portionwise over 20 min at 0° C. After stirring for 15 at room temperature, the solvent was removed under reduced pressure. Water (20 ml) and ethyl acetate (40 ml) were added to the solid residue. The resulting mixture was filtered through a celite bed which was washed with ethyl acetate (20 ml). After collecting the filtrate, the organic phase was separated, dried over Na2SO4 and the solvent removed under reduced pressure to afford amine 51 as an off white solid (0.596 g, 1.83 mmol, 87%). The amine was used in the next step without further purification.

後処理

  1. customthe solvent was removed under reduced pressure
  2. additionWater (20 ml) and ethyl acetate (40 ml) were added to the solid residue
  3. filtrationThe resulting mixture was filtered through a celite bed which
  4. washwas washed with ethyl acetate (20 ml)
  5. customAfter collecting the filtrate
  6. customthe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-8545c269d1274ba1afb037607ca971e0
出典データセット
uspto-grants-2011_06
特許番号
US07960434B2

反応ノート

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