Water → 4-Nitrobenzyl (2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylate

HRID 1194941Notes

Reaction equation

HRID 1194941 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([C:20]([OH:22])=[O:21])[CH2:3]1.[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])[C@H:4]([C:20]([O:22][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)=[O:21])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

Product 1

HCID 136446194-Nitrobenzyl (2S,4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid (930 mg, 3 mmol), 4-nitrobenzylbromide (660 mg, 3.05 mmol) and potassium carbonate (209 mg, 1.51 mmol) were stirred together in N,N-dimethylformamide (lOml) for 3.5 h. The mixture was poured into water (100 ml)/ethyl acetate (100 ml) and the layers separated. The aqueous layer was re-extracted with ethyl acetate (50 ml). The combined organic layers were washed with water (50 ml),×4), brine (20 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with ethyl acetate hexane mixture, followed by ethyl acetate to give the title compound (1.20 g, 90%) as a mixture of conformers/rotamers; νmax (CH2Cl2) 3610, 3470, 2960, 1735, 1710, 1610, 1535, and 1350 cm-1 ; δH (400 MHz, CDCl3) 1.90 (1H, broad d, J ca 7.4 Hz), 2.05-2.20 (1H, m), 2.3-2.5 (1H, m), 3.6-3.8 (2H, m), 4.58 (1H, broad d, J ca 9.3 Hz), 4.63 (1H, approx dt J 1.9, 8.1 Hz), 5.05-5.35 (4H, m,) 7.30-7.50 (4H, m), and 8.1-8.2 (4H, m); [Mass spectrum: M+ (445)].

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was re-extracted with ethyl acetate (50 ml)
  3. washThe combined organic layers were washed with water (50 ml),×4), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluting with ethyl acetate hexane mixture

Sources & evidence

ORD record
ord-cd7fd54efe9e448bbeeb041ccf109cbd
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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