5-Fluoro-2-nitrophenol → (2S,4S)-1-tert-butyl 2-methyl 4-(5-fluoro-2-nitrophenoxy)pyrrolidine-1,2-dicarboxylate

HRID 240596Notes

Reaction equation

HRID 240596 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15](=[O:29])[C@@H:16]1[CH2:20][C@@H:19]([OH:21])[CH2:18][N:17]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[F:30][C:31]1[CH:32]=[CH:33][C:34]([N+:38]([O-:40])=[O:39])=[C:35](O)[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:30][C:31]1[CH:36]=[CH:35][C:34]([N+:38]([O-:40])=[O:39])=[C:33]([CH:32]=1)[O:21][C@@H:19]1[CH2:18][N:17]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@H:16]([C:15]([O:14][CH3:13])=[O:29])[CH2:20]1

Participants

6

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 58413039(2S,4S)-1-tert-butyl 2-methyl 4-(5-fluoro-2-nitrophenoxy)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diethylazodicarboxylate (1.76 ml) was added dropwise to a solution of N-Boc-trans-4-hydroxy-L-proline methyl ester (2.74 g), 5-fluoro-2-nitrophenol (1.47 g) and triphenylphosphine (2.93 g) in dichlormethane under cooling at 0° C. The coolant was removed after 20 min and the reaction mixture was stirred at room temperature over the weekend. The solvent was evaporated and the residue war purified by chromatography to give the desired product.

Workup

  1. customThe coolant was removed after 20 min
  2. customThe solvent was evaporated
  3. customthe residue war purified by chromatography

Sources & evidence

ORD record
ord-c3706526ba5e40f2a807010243d86d46
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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