Potassium Cyanide → HCID 131724856, compound

HRID 2180226Notes

Reaction equation

HRID 2180226 reaction equation
[CH:1]1([CH2:7][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(O)[O-].[Na+].[C-:24]#[N:25].[K+]>O.C(OCC)(=O)C>[C:24]([CH:9]([OH:10])[C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)#[N:25]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 13825239HCID 13825239, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 131724856HCID 131724856, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 1B (19.7 g, 77.1 mmol) and sodium bisulfite (8.0 g, 77.1 mmol) in water (500 mL) at 5° C. was stirred for 24 hours, warmed to room temperature, treated with a solution of potassium cyanide (5.1 g, 78.8 mmol) in ethyl acetate (350 mL), and stirred for 5 hours. The aqueous phase was separated and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide tert-butyl (1R)-2-cyano-1-(cyclohexylmethyl)-2-hydroxyethylcarbamate.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25f881fe828947f99e8f3ba1bba6a190
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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