HCID 59293622, compound → HCID 59293613, compound

HRID 872081Notes

Reaction equation

HRID 872081 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][C:17]([C:23]([F:26])([F:25])[F:24])=[CH:16][C:15]=2[N+:27]([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][C:14]2[C:15]([NH2:27])=[CH:16][C:17]([C:23]([F:24])([F:25])[F:26])=[CH:18][C:19]=2[NH2:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59293622HCID 59293622, compound

Product 1

HCID 59293613HCID 59293613, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

The product from Step 1 is dissolved in methanol and hydrogenated at 100-200 psi and 30-50° C. in the presence of 10% Pd/C until the reduction is deemed complete by HPLC. The reaction mixture is filtered through Celite. The filtrate is concentrated and dried to afford (R)-3-(2,6-diamino-4-trifluoromethylphenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester which can be used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationThe filtrate is concentrated
  3. customdried

Sources & evidence

ORD record
ord-042f52a31a564c2da8939143482e2da3
Source dataset
uspto-grants-2015_03
Patent number
US08975262B2

Reaction notes

Loading…