Benzyl Alcohol → (1-Phenyl-cyclohexyl)-carbamic acid benzyl ester

HRID 2235198노트

반응식

HRID 2235198 반응식
[C:1]1([C:7]2(C(O)=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC=CC=1>[CH2:40]([O:47][C:21](=[O:30])[NH:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 708171-Phenylcyclohexane-1-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

생성물 1

HCID 59299316(1-Phenyl-cyclohexyl)-carbamic acid benzyl ester수율 38%

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
80 °C

실험 절차

Dissolve 1-phenyl-cyclohexanecarboxylic acid (5.0 g, 24.48 mmol) in benzene (200 mL). Add triethylamine (2.45 g, 24.48 mmol), diphenylphosphoryl azide (6.74 g, 24.48 mmol), and benzyl alcohol (3.97 g, 36.72 mmol) under nitrogen. Stir and heat the reaction mixture to 80° C. Continue to heat the reaction at 80° C. for 8 hours, then cool to room temperature. Add water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane) to give 2.87 g (38%) of the title compound as a colorless oil.

후처리

  1. temperatureto heat
  2. customthe reaction at 80° C. for 8 hours
  3. temperaturecool to room temperature
  4. extractionAdd water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-2fbe188cdd314f84b899a53aec685cf6
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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