Potassium Cyanide → HCID 59026120, compound

HRID 639082Notes

Reaction equation

HRID 639082 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C-:17]#[N:18].[K+].OS([O-])=O.[Na+]>C1COCC1.O>[C:17]([C:2]1([OH:1])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)#[N:18]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 5612031-N-Cbz-3-pyrrolidinoneHCID 23665763Sodium Bisulfite

Product 1

HCID 59026120HCID 59026120, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenylmethyl 3-oxo-1-pyrrolidinecarboxylate (1.0 g, 4.56 mmole) and KCN (0.81 g, 12.54 mmole) in THF (5 mL) and H2O (15 mL) at 0° C. was added NaHSO3 (1.14 g, 10.9 mmole) in H2O (5.0 mL). After 3 h, the reaction contents were concentrated in vacuo, extracted with CHCl3 (2×100 mL), and the organics dried over Na2SO4. Purification on silica (hexanes/EtOAc, 1:1) afforded the title compound (0.92 g, 82%) as a light yellow oil: LC-MS (ES) m/e 247 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationwere concentrated in vacuo
  3. extractionextracted with CHCl3 (2×100 mL)
  4. dry with materialthe organics dried over Na2SO4
  5. customPurification on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-3de2341293bc45f493d5c0cda14739b6
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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