Diethyl (cyanomethyl)phosphonate → HCID 178453883, compound

HRID 711959Notes

Reaction equation

HRID 711959 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1)=O>O1CCCC1>[C:7]([CH:9]=[CH:18][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1)#[N:8]

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 178453955HCID 178453955, compound

Product 1

HCID 178453883HCID 178453883, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1.0 M potassium tert-butoxide in THF (1.0 mL, 1.0 mmol) was added diethyl cyanomethylphosphonate (0.15 mL, 0.92 mmol) dropwise at 0° C. and the resulting mixture was stirred at 0° C. for 1 h. A solution of tert-butyl (trans-4-formylcyclohexyl)carbamate (0.15 g, 0.66 mmol) (Example 5, Step 1) in tetrahydrofuran (4.6 mL) was added dropwise, then cooling bath was removed and the reaction mixture was stirred at room temperature for 1 h. The reaction was diluted with EtOAc, washed with water. The organic layers were concentrated and purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product as a mixture of E- and Z-isomers (0.14 g, 70%). LCMS calculated for C14H22N2O2Na (M+Na)+: m/z=273.2. Found: 273.0.

Workup

  1. temperaturecooling bath
  2. customwas removed
  3. stirringthe reaction mixture was stirred at room temperature for 1 h
  4. additionThe reaction was diluted with EtOAc
  5. washwashed with water
  6. concentrationThe organic layers were concentrated
  7. custompurified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-d2bc4766468e4fbba87b99ff6e34482b
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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