Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Phenylmethyl 3,3-dimethyl-2-(methyloxy)-1-pyrrolidinecarboxylate

HRID 1014154Notes

Reaction equation

HRID 1014154 reaction equation
[OH:1][CH:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[C:19]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH3:7][C:6]1([CH3:8])[CH2:5][CH2:4][N:3]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH:2]1[O:1][CH3:19]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57878117Phenylmethyl 2-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate

Product 1

HCID 57878094Phenylmethyl 3,3-dimethyl-2-(methyloxy)-1-pyrrolidinecarboxylateYield 895.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

In a 500 ml flask was dissolved phenylmethyl 2-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate (0.0475 mol, 11.8 g) in 100 ml methanol. Catalytic Pyridinium p-toluenesulfonate (0.00475 mol, 1.19 g) was added and the reaction was stirred at 20° C. for 45 min. The reaction was quenched with triethylamine (3 ml) and concentrated. The resulting crude oil was purified on 120 g silica (chloroform/ethyl acetate) yielding 11.2 g (90%) of phenylmethyl 3,3-dimethyl-2-(methyloxy)-1-pyrrolidinecarboxylate as a clear oil. LCMS (ESI+)=286 m/z (MNa+). 1H NMR (400 MHz, CDCl3)— rotomers δ 7.39-7.32 (m, 5H), 5.24-5.13 (m, 2H), 4.68 and 4.57 (s, 1H), 3.52-3.46 (m, 4H), 3.31 (s, 2H), 1.97-1.90 (m, 1H), 1.58-1.54 (m, 1H), 1.10 (s, 3H), 0.9 (s, 3H).

Workup

  1. customThe reaction was quenched with triethylamine (3 ml)
  2. concentrationconcentrated
  3. customThe resulting crude oil was purified on 120 g silica (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-c45e8f92f94e49dd82c4c85d341e68ef
Source dataset
uspto-grants-2011_07
Patent number
US07982053B2

Reaction notes

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