Sodium Cyanide → HCID 178519557, compound

HRID 970724Notes

Reaction equation

HRID 970724 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH2:9][CH:10]([CH2:14][CH:15]=O)[CH2:11][CH2:12][CH:13]=1)(C)(C)C.S([CH2:29][N+:30]#[C-:31])(C1C=CC(C)=CC=1)(=O)=O.[C-]#N.[Na+].CCCC[N+:39](CCCC)(CCCC)CCCC.[F-]>CCO.C1COCC1>[NH:30]1[CH:31]=[C:15]([CH2:14][CH:10]2[CH2:9][C:8]([CH2:7][OH:6])=[CH:13][CH2:12][CH2:11]2)[N:39]=[CH:29]1

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 161915Tosylmethyl isocyanideHCID 2724141Tetrabutylammonium FluorideHCID 131726104[3-(Tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enyl]-acetaldehyde

Product 1

HCID 178519557HCID 178519557, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The following preparation followed the procedure by Horne et al., Heterocycles 39:139 (1994). A solution of the aldehyde (Intermediate R5; 0.34 g, 1.3 mmol) in EtOH (5 mL) was treated with tosylmethyl isocyanide (TosMIC; Aldrich; 0.25 g; 1.3 mmol) and NaCN (˜15 mg, cat) and allowed to stir at room temperature for 20 minutes. The solvent was removed in vacuo; the residue was dissolved in ˜7M NH3 in MeOH and transferred to a resealable tube before heating at 100° C. for 15 hours. The mixture was concentrated and purified by chromatography on SiO2 with 5% MeOH (sat. w/NH3):CH2Cl2. A solution of the product in THF with TBAF (1.5 eq.) was stirred at room temperature after aqueous workup. The crude product was chromatographed (5-7% NH3/MeOH in CH2Cl2) and designated Compound 2.

Workup

  1. customThe following preparation
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ˜7M NH3 in MeOH
  4. customtransferred to a resealable tube
  5. temperaturebefore heating at 100° C. for 15 hours
  6. concentrationThe mixture was concentrated
  7. custompurified by chromatography on SiO2 with 5% MeOH (sat. w/NH3)
  8. customThe crude product was chromatographed (5-7% NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ee70b1ab07174b54976f161ca9aab9e2
Source dataset
uspto-grants-2007_12
Patent number
US07312238B2

Reaction notes

Loading…