Methylparaben → HCID 11171084, compound

HRID 354455Notes

Reaction equation

HRID 354455 reaction equation
[C:1]([O:5]C(N1C[C@@H](N(C)C)C[C@H]1CO)=O)(C)(C)C.O[C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:23]([O:25][O:5][CH3:1])(=[O:24])[C:22]1[CH:27]=[CH:28][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 69333213HCID 69333213, compound

Product 1

HCID 11171084HCID 11171084, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of cis-1-tert-butoxycarbonyl-4-dimethylamino-(2S)-hydroxymethylpyrrolidine (555 mg, 2.27 mmol), methyl 4-hydroxybenzoate (380 mg, 2.5 mmol), and Ph3P (1.07 g, 4.09 mmol) in THF (10 ml) was added DIAD (826 mg, 4.09 mmol) at 0° C. The reaction mixture was stirred at 70° C. for 18 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (1/2, v/v) MeOH—CH2Cl2(5/95, v/v) as eluent to give methyl 4cis-1-tert-butoxycarbonyl diethylamino-(2S)-pyrrolidinyl)methoxy benzoate (260 mg, 30%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.45 (s, 9H), 1.70-1.90 (m, 1H), 2.26 (s, 6H), 2.33 (m, 1H), 2.57 (m, 1H), 3.06 (m, 1H) 3.85-4.23 (m, 4H), 388 (s, 3H), 6.93 (m, 2H), 7.95 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel with n-hexane-EtOAc (1/2

Sources & evidence

ORD record
ord-87648aaa45a941a19d4ad393e1d07cbe
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…