Potassium Iodide → (R)-3-(4-nitro-3-trifluoromethyl-phenylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 511200Notes

Reaction equation

HRID 511200 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([C:24]([F:27])([F:26])[F:25])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([C:24]([F:25])([F:27])[F:26])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 58576068(R)-3-(4-nitro-3-trifluoromethyl-phenylamino)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(R)-3-Amino-pyrrolidine-1-carboxylic acid tert-butyl ester (559 mg; 3.0 mmol), 4-fluoro-1-nitro-2-trifluoromethyl-benzene (627 mg; 3.0 mmol), potassium carbonate (1.24 g; 9.0 mmol), potassium iodide (498 mg; 3.0 mmol), acetonitrile (6 mL) and water (2 mL) are mixed together and the resulting reaction mixture heated to efflux for 5 hours. The phases are separated and the organic phase dried (MgSO4) and concentrated under high vacuum. The residue is then triturated with diethyl ether, dried under high vacuum to afford the desired compound (1.12 g; 2.98 mmol).

Workup

  1. customthe resulting reaction mixture
  2. temperatureheated to efflux for 5 hours
  3. customThe phases are separated
  4. dry with materialthe organic phase dried (MgSO4)
  5. concentrationconcentrated under high vacuum
  6. customThe residue is then triturated with diethyl ether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-f08bba484fb3443ead0969f4ddd6f62b
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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