Ethanol → HCID 67054475, compound

HRID 2092650Notes

Reaction equation

HRID 2092650 reaction equation
CC([O-])(C)C.[K+].[C:7]([O:11][C:12](=[O:26])[NH:13][CH2:14][C:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH:18]3O)[CH2:16]1)[CH2:22]2)([CH3:10])([CH3:9])[CH3:8].CC1C=CC(S([CH2:37][N+:38]#[C-])(=O)=O)=CC=1.CCO>COCCOC>[C:7]([O:11][C:12](=[O:26])[NH:13][CH2:14][C:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH:18]3[C:37]#[N:38])[CH2:16]1)[CH2:22]2)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 58192779HCID 58192779, compound

Product 1

HCID 67054475HCID 67054475, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Solid t-BuOK (240 mg, 2.15 mmol) was added as 6 portions to a solution of ketone 1B (300 mg, 1.07 mmol) and TosMIC (273 mg, 1.40 mmol) in a mixture of DME (5.0 mL) and absolute EtOH (1 mL) while keeping the temperature between 5 and 10° C. The reaction mixture was allowed to warm to rt and was maintained for 30 min. The reaction mixture was then heated at 35-40° C. for 30 min and was then allowed to cool to rt. The precipitate (TosK) was removed by filtration and the filter cake was washed with DME. The combined organic layers were concentrated and the residue was purified by column chromatography (0/100 to 10/90 MeOH/EtOAc) to provide nitrile 17A (203 mg, 70%) as a mixture of equatorial and axial isomers. Data: LC/MS (ESR) m/z=291 [M+H]+.

Workup

  1. customthe temperature between 5 and 10° C
  2. temperaturewas maintained for 30 min
  3. temperatureThe reaction mixture was then heated at 35-40° C. for 30 min
  4. temperatureto cool to rt
  5. customThe precipitate (TosK) was removed by filtration
  6. washthe filter cake was washed with DME
  7. concentrationThe combined organic layers were concentrated
  8. customthe residue was purified by column chromatography (0/100 to 10/90 MeOH/EtOAc)

Sources & evidence

ORD record
ord-5422fe9bc0d447f9a2165a27ec1bb188
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

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