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

HRID 1169603노트

반응식

HRID 1169603 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3fd5e52718b4ec9a4f3d61d45542ebb
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825120B2

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