4-Nitrobenzoic Acid → Phenylmethyl(cis)-3-methyl-4-{[(4-nitrophenyl)carbonyl]oxy}-1-pyrrolidinecarboxylate

HRID 1366481Notes

Reaction equation

HRID 1366481 reaction equation
[OH:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:7][C@H:6]1[C@@H:2]([O:1][C:25]([C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:29][CH:28]=2)=[O:26])[CH2:3][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5]1

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58277775benzyl (3S,4R)-3-hydroxy-4-methylpyrrolidine-1-carboxylate

Product 1

HCID 86636955Phenylmethyl(cis)-3-methyl-4-{[(4-nitrophenyl)carbonyl]oxy}-1-pyrrolidinecarboxylateYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of enantiopure phenylmethyl (trans)-3-hydroxy-4-methyl-1-pyrrolidinecarboxylate (E1) (1 g, 4.25 mmol) in THF (21 mL) was added 4-nitrobenzoic acid (1.42 g, 8.5 mmol), triphenylphosphine (2.23 g, 8.5 mmol) and DIAD (1.7 mL, 8.5 mmol). The resulting solution was stirred overnight. Removal of the solvent under reduced pressure yielded the crude product which was purified by RP-HPLC yielding phenylmethyl (cis)-3-methyl-4-{[(4-nitrophenyl)carbonyl]oxy}-1-pyrrolidinecarboxylate (1.30 g, 79%). LCMS: (M+H)+: 385.0 (single unknown enantiomer).

Workup

  1. customRemoval of the solvent under reduced pressure
  2. customyielded the crude product which
  3. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-6507dc23728845e2bb485e176e6791cc
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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