Hydrochloric Acid → (S)-tert-butyl 4-(3-(1-hydroxyethyl)benzyl)piperazine-1-carboxylate

HRID 1169603ノート

反応式

HRID 1169603 の反応式
N#N.C(N(CC)C1C=CC=CC=1)C.B.[C:15]([C:18]1[CH:19]=[C:20]([CH:36]=[CH:37][CH:38]=1)[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)=O)(=[O:17])[CH3:16].Cl>C1(C)C=CC=CC=1.CO>[OH:17][C@H:15]([C:18]1[CH:19]=[C:20]([CH:36]=[CH:37][CH:38]=1)[CH2:21][N:23]1[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:27][CH2:28]1)[CH3:16]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 83312Diethylaniline-boraneHCID 68765074Tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate

生成物 1

HCID 68766191(S)-tert-butyl 4-(3-(1-hydroxyethyl)benzyl)piperazine-1-carboxylate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒3 回

実験手順

Under a positive pressure of N2 1-1.5M solution of (S)-Methyl oxazaborolidine (0.5 mL, 5.0 mmol) was diluted in 2 mL of toluene and treated with 3.6 mL of borane-N,N-diethylaniline. The tert-butyl 4-(3-acetylbenzoyl)piperazine-1-carboxylate from above in 3 mL of anhydrous toluene was added to the above solution over 1 hour and stirred for an additional hour. The mixture was stirred at 20° C. for another hour. To the mixture was added 6 mL MeOH, 12 mL 1N HCl and the resultant mixture stirred for 20 min. The mixture was diluted with 50 mL toluene and washed with saturated NaCl (50 mL). The organic extracts were dried over Na2SO4, filtered and concentrated at reduced pressure. The residue was heated at reflux in Et2NH for 1 hour. Purification by reverse-phase HPLC to afforded (S)-tert-butyl 4-(3-(1-hydroxyethyl)benzyl)piperazine-1-carboxylate as 1.08 g of white solid.

後処理

  1. stirringThe mixture was stirred at 20° C. for another hour
  2. washwashed with saturated NaCl (50 mL)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. temperatureThe residue was heated
  7. temperatureat reflux in Et2NH for 1 hour
  8. customPurification by reverse-phase HPLC

出典と根拠

ORDレコード
ord-a3fd5e52718b4ec9a4f3d61d45542ebb
出典データセット
uspto-grants-2010_11
特許番号
US07825120B2

反応ノート

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