HCID 86724664, compound → HCID 86724663, compound

HRID 1486263Notes

Reaction equation

HRID 1486263 reaction equation
[C:1]([C:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH2:4][F:5])#[N:2].[H][H]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:6])[CH2:4][F:5]

Participants

6

Reactant 2

HCID 86724664HCID 86724664, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86724663HCID 86724663, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Under argon, 1.2 g (5.08 mmol) of rac-benzyl (2-cyano-1-fluoropropan-2-yl)carbamate from Example 54A in 14.9 ml of 7 N ammonia in methanol were admixed with 1.55 g of Raney nickel (aqueous slurry) and hydrogenated at hydrogen pressure about 25 bar and RT for 24 hours. The reaction mixture was filtered through kieselguhr, washed with methanol and concentrated. 1.2 g of the target compound were obtained (98% of theory).

Workup

  1. filtrationThe reaction mixture was filtered through kieselguhr
  2. washwashed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-538bd69bb69d4976ab2fcc7cf29ba814
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

Loading…