Benzyl Alcohol → Benzyl 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-ylcarbamate

HRID 1993379Notes

Reaction equation

HRID 1993379 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12](C(O)=O)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC[N:29]([CH2:32]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([NH:29][C:32](=[O:41])[O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 433803921-(3-Fluoro-4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 57445404Benzyl 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidine-3-carboxylic acid (1.5 g, 5.92 mmol), BnOH (1.92 g, 17.76 mmol), Et3N (1.24 mL, 8.88 mmol) and DPPA (1.84 g, 7.12 mmol) in 100 mL of toluene was heated to 120° C. for 6 h. The reaction was cooled to RT and concentrated in vacuo. The residue was purified by chromatography on a silica gel column (10% to 70% EtOAC/hexane) to give the title compound as colorless crystal. MS (ESI pos. ion) m/z: 359.4 (M+H). Calc'd Exact Mass for C19H19FN2O4: 358.36.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column (10% to 70% EtOAC/hexane)

Sources & evidence

ORD record
ord-90400b49c710436e828e4eaccb3d4101
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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