Tosylmethyl isocyanide → HCID 117706781, compound

HRID 1778557Notes

Reaction equation

HRID 1778557 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH:14]([OH:16])[CH2:15][CH:9]1[CH2:10][C:11](=O)[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([CH2:28][N+:29]#[C-])(=O)=O)=CC=1.CC([O-])(C)C.[K+]>COCCOC.CCO>[CH2:1]([N:8]1[CH:13]2[CH:14]([OH:16])[CH2:15][CH:9]1[CH2:10][CH:11]([C:28]#[N:29])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 21699645HCID 21699645, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 117706781HCID 117706781, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 8-benzyl-6-hydroxy-8-azabicyclo[3.2.1]octan-3-one (1.2 g) and TosMIC (1.95 g) in a mixture of 20 mL of DME and 0.5 mL of absolute EtOH was added t-BuOK (3.5 g) portionwise while keeping the temperature between 5 and 10° C. The resulting mixture was stirred at room temperature 30 min, and then warmed to 35-40° C. for another 30 minutes. The suspension thus obtained was cooled to room temperature, and the precipitate (TosK) was removed and extracted with DME. The combined DME solutions were concentrated to 3 mL and purified by silica gel chromatography to give 8-benzyl-6-hydroxy-8-azabicyclo[3.2.1]octane-3-carbonitrile 150b (0.8 g).

Workup

  1. customthe temperature between 5 and 10° C
  2. temperaturewarmed to 35-40° C. for another 30 minutes
  3. customThe suspension thus obtained
  4. temperaturewas cooled to room temperature
  5. customthe precipitate (TosK) was removed
  6. extractionextracted with DME
  7. concentrationThe combined DME solutions were concentrated to 3 mL
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-71d3aacb1bb548cfa2ae395be1b790e8
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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