Triphenylphosphine → Racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

HRID 229796

反応式

HRID 229796 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]([N:30]1[CH2:36][CH:35]([OH:37])[CH:34]([N:38]=[N+]=[N-])[CH2:33][CH2:32][CH:31]1[CH3:41])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.O.C1(C)C=CC=CC=1>[CH2:20]([O:27][C:28]([N:30]1[CH2:36][CH:35]([OH:37])[CH:34]([NH2:38])[CH2:33][CH2:32][CH:31]1[CH3:41])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

6

反応物 2

HCID 11776TriphenylphosphineHCID 21036431Racemic (2R,5S,6S)-5-Azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

生成物 1

HCID 21036430Racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

Triphenylphosphine (1.94 g, 7.4 mmol) was added to a solution of racemic (2R,5S,6S)-5-azido-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (1.5 g, 4.93 mmol) in THF (185 ml) and H2O (0.7 ml), then was heated to 45 degrees C. overnight. The reaction mixture was then diluted with toluene (100 ml×2) and was azeotroped in vacuo by rotary evaporation twice. The resxulting oil was dissolved in MeOH and HCl in Et2O and the resulting salt was collected following filtration and was used in the next reaction without further purification (1.4 g, 90%).

後処理

  1. customovernight
  2. customwas azeotroped in vacuo by rotary evaporation twice
  3. dissolutionThe resxulting oil was dissolved in MeOH
  4. customHCl in Et2O and the resulting salt was collected
  5. filtrationfiltration
  6. customwas used in the next reaction without further purification (1.4 g, 90%)

出典と根拠

ORDレコード
ord-659e292adbee42fc808784a739c17ac0
出典データセット
uspto-grants-2009_07
特許番号
US07563784B2

関連ノート

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