Diethyl (cyanomethyl)phosphonate → tert-Butyl {3-[2-cyanovinyl]cyclohexyl}carbamate

HRID 712037노트

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HRID 712037 반응식
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21]1)=O>O1CCCC1>[C:7]([CH:9]=[CH:18][CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21]1)#[N:8]

참가 물질

5

반응물 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 86717490tert-Butyl N-(3-formylcyclohexyl)carbamate

생성물 1

HCID 86717491tert-Butyl {3-[2-cyanovinyl]cyclohexyl}carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To 1.0 M potassium tert-butoxide in THF (2.0 mL, 2.0 mmol) was added diethyl cyanomethylphosphonate (0.30 mL, 1.8 mmol) dropwise at 0° C. and the mixture was stirred at 0° C. for 1 h. A solution of tert-butyl (3-formylcyclohexyl)carbamate (0.30 g, 1.3 mmol) in tetrahydrofuran (9.3 mL) was added dropwise, then cooling bath was removed, and the mixture was stirred at room temperature overnight. The mixture was diluted with EtOAc, washed with water, concentrated and purified on silica gel column (eluting with 0-30% EtOAc in hexanes) to give the desired product as a mixture of cis- and trans-isomer mixtures (0.12 g, 36%). LCMS calculated for C14H22N2O2Na (M+Na)+: m/z=273.2. Found: 273.1.

후처리

  1. temperaturecooling bath
  2. customwas removed
  3. stirringthe mixture was stirred at room temperature overnight
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with water
  6. concentrationconcentrated
  7. custompurified on silica gel column (eluting with 0-30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a7ef6578c94145b298ec38ddc04e0045
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181271B2

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