Sodium Cyanide → HCID 59271815, compound

HRID 1893206Notes

Reaction equation

HRID 1893206 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([O:15][CH3:16])[CH2:11][CH2:12][CH:13]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([NH2:19])[CH3:18].Cl.[C-:21]#[N:22].[Na+].[CH3:24][C:25]([O:28][C:29]([O:31]C(OC(C)(C)C)=O)=O)([CH3:27])[CH3:26]>O1CCOCC1.C([O-])(O)=O.[Na+].CCOC(C)=O.O>[C:25]([O:28][C:29](=[O:31])[N:19]([CH:13]([C:21]#[N:22])[CH2:12][CH2:11][C@H:10]([O:15][CH3:16])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][CH3:18])([CH3:27])([CH3:26])[CH3:24]

Participants

9

Reactant 4

HCID 8929Sodium CyanideHCID 11198Ethylamine hydrochlorideHCID 90495Di-tert-butyl dicarbonateHCID 59271849HCID 59271849, compound

Product 1

HCID 59271815HCID 59271815, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (4S)-5-(benzyloxy)-4-methoxypentanal (109 g, 490 mmol) in dioxane (500 mL) at room temperature was added EtNH2.HCl (60 g, 736 mmol), NaCN (36 g, 736 mmol), and H2O (500 mL). The reaction mixture was stirred for 2 days, then diluted with saturated aqueous NaHCO3 and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. To a solution of the crude residue in EtOAc (500 mL) was added (Boc)2O (107 g, 492 mmol). The resulting mixture was stirred at 40° C. for 2 days. The reaction mixture was cooled to ambient temperature, diluted water, and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography eluted with 10 to 40% EtOAc in hexanes provided tert-butyl[(4S)-5-(benzyloxy)-1-cyano-4-methoxypentyl]ethylcarbamate. LC-MS: 377.4 (M+1).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. stirringThe resulting mixture was stirred at 40° C. for 2 days
  6. extractiondiluted water, and extracted with EtOAc (3×)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. washFlash column chromatography eluted with 10 to 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-aedd462671b3435b93ee5a843a093150
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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