Methylparaben → HCID 20737849, compound

HRID 354446Notes

Reaction equation

[C:1]([N:8]1[C@H:12]([CH3:13])[CH2:11][CH2:10][C@H:9]1[CH2:14][OH:15])([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:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:1]([N:8]1[C@H:12]([CH3:13])[CH2:11][CH2:10][C@H:9]1[CH2:14][O:15][C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

Reactant 4

HCID 7456Methylparaben

HCID 11776Triphenylphosphine

HCID 75555Diisopropyl diazene-1,2-dicarboxylate

HCID 20737857HCID 20737857, compound

Product 1

HCID 20737849HCID 20737849, compoundYield 99.2%

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of N-Boc-2-(S)-hydroxymethyl-5-(R)-methylpyrrolidine (820 mg, 3.81 mmol), triphenylphosphine (1.10 g, 4.19 mmol) and methyl 4-hydroxybenzoate (580 mg, 3.81 mmol) was added diisopropyl azodicarboxylate (841 ml, 4.19 mmol) at rt, and the resulting mixture was stirred at 60° C. for 1 h. The mixture was concentrated in vacuo, and the residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent to give methyl 4-[N-Boc-5-(R)-methyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.32 g, 80%) as a colorless oil. 1H-NMR (CDCl3) δ1.24 (brs, 3 H), 1.49 (s, 9 H), 1.55-1.70 (m, 2 H), 1.94-2.11 (m, 2 H), 3.88 (s, 3 H), 3.88 (overlap, 1H), 4.06-4.20 (m, 2H), 6.93-6.96 (m, 2H), 7.97 (d, J=8.8 Hz, 2 H); MS (ESI) m/z, 350 (M++H).

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent

Sources & evidence

ORD record: ord-2301f1abd9ba45bd91224372462e788b
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756378B2

Reaction notes

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