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

HRID 1780000

反応式

HRID 1780000 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad5952ecb9cf4d2fa103276c0c41a12a
出典データセット
uspto-grants-1997_05
特許番号
US05629322

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