Ammonium formate → 1-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl(alpha-methyl-4-methoxyphenethyl)amino]ethanol

HRID 572703ノート

反応式

HRID 572703 の反応式
[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:12]([CH:13]([OH:34])[CH2:14][N:15]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:16]([CH3:26])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:10]=1[N+:37]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd]>[NH2:37][C:10]1[CH:11]=[C:12]([CH:35]=[CH:36][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:13]([OH:34])[CH2:14][N:15]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:16]([CH3:26])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

参加物

4

反応物 2

HCID 2723923Ammonium formateHCID 9914834α-[[[2-(4-Methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-3-nitro-4-(phenylmethoxy)benzenemethanol

生成物 1

HCID 543359181-[3-Amino-4-(benzyloxy)phenyl]-2-[benzyl(alpha-methyl-4-methoxyphenethyl)amino]ethanol

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
40 °C

実験手順

To a solution of 4-benzyloxy-3-nitro-α-[N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)aminomethyl]benzyl alcohol (100 gms, 0.19 M) in SPDS (1.0 lit) was added 10% Pd/C. The resulting mass was heated to 40° C. and ammonium formate (36 gms, 0.57 M) was added in lots in 1 hour. The reaction mass was heated slowly to 70° C. for 1 hour, and then cooled to 50° C. The catalyst was removed by filtration and the clear filtrate evaporated. The residue was stirred in water (500 ml) and basified with liq. Ammonia. The reaction mass was extracted in 1.0-lit toluene, washed organic extract with water, dried on sodium sulfate and evaporated to obtain title compound. (78 gms, 83%)

後処理

  1. temperatureThe reaction mass was heated slowly to 70° C. for 1 hour
  2. temperaturecooled to 50° C
  3. customThe catalyst was removed by filtration
  4. customthe clear filtrate evaporated
  5. extractionThe reaction mass was extracted in 1.0-lit toluene
  6. washwashed organic
  7. extractionextract with water
  8. customdried on sodium sulfate
  9. customevaporated

出典と根拠

ORDレコード
ord-d284eec7e3b34bfdabbeb552d277fce3
出典データセット
uspto-grants-2015_05
特許番号
US09029421B2

反応ノート

読み込み中…