Benzyl Alcohol → (R)-N-Cbz-2,6-dimethyl-5-hepten-1-amine

HRID 1780000

반응식

HRID 1780000 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C(O)(=O)[CH2:19][C@@H:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH3:21].C([N:32]([CH2:35]C)CC)C.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:21][C@H:20]([CH2:22][CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])[CH2:19][NH:32][C:35]([O:44][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:8]

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6999957(R)-(+)-citronellic acid

생성물 1

HCID 22872580(R)-N-Cbz-2,6-dimethyl-5-hepten-1-amine수율 60.3%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Diphenylphosphoryl azide (14 mL, 65 mmol) was added dropwise to a solution of (R)-citronellic acid (10 g, 59 mmol) and triethylamine (9.1 mL, 65mmol) in 60 mL of toluene. The mixture was heated for 1 hr at 80° C. 12 mL (120 mmol) of benzyl alcohol was added and the mixture was heated to reflux for 4 hrs. The reaction mixture was cooled, diluted with ethyl acetate and washed with water, saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was removed in vacuo to give a crude product which was purified on silica gel using 5% ethyl acetate in hexane as solvent to afford 9.8 g of the desired carbamate as a thick oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hrs
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water, saturated sodium chloride solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give a crude product which
  8. customwas purified on silica gel using 5% ethyl acetate in hexane as solvent

출처 및 근거

ORD 기록
ord-ad5952ecb9cf4d2fa103276c0c41a12a
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629322

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