Methylparaben → HCID 20737850, compound

HRID 354440Notes

Reaction equation

HRID 354440 reaction equation
[C:1]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@H:9]1[CH2:19][OH:20])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:1]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@H:9]1[CH2:19][O:20][C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 207378581-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-5-phenyl-, 1,1-dimethylethyl ester, (2S,5R)-

Product 1

HCID 20737850HCID 20737850, compoundYield 80.2%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-Boc-2-(S)-hydroxymethyl-5-(R)-phenylpyrrolidine (1.10 g, 3.97 mmol), triphenylphosphine (1.25 g, 4.76 mmol) and methyl 4-hydroxybenzoate (724 mg, 4.76 mmol) was added diisopropyl azodicarboxylate (955 ml, 4.76 mmol) at rt, and the resulting mixture was stirred at 60° C. for 45 min. The mixture was concentrated in vacuo, and the residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give methyl 4-[N-Boc-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.31 g, 80%) as a colorless oil. 1H-NMR (CDCl3) δ1.19 and 1.47 (brs, total 9 H), 2.09-2.15 (m, 3 H), 2.33-2.37 (m, 1 H ), 3.94 (s, 3 H), 4.30 (brs, 1 H), 4.41 (brs, 2 H), 4.77 (brs, 1 H), 7.03 (d, J=8.8 Hz, 2 H), 7.24-7.36 (m, 5 H), 8.03-8.06 (m, 2 H); MS (ESI) m/z, 412 (M++H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-ebb1f6490bb249a391812961cc0283b1
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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