Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate

HRID 1175133Notes

Reaction equation

HRID 1175133 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[CH:17][C:15]([O:14][CH3:13])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 56923823tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Oxo-azetidine-1-carboxylic acid tert-butyl ester (1.67 g; 9.7 mmol) and methoxycarbonyl-methylene-triphenylphosphorane (3.42 g; 10.25 mmol) are dissolved in toluene (5 ml), refluxed for 2.5 hours and left over night at room temperature. The precipitate is filtered off, washed with TBME, and the filtrate purified via chromatography (TBME/hexane 2:8>3:7) to yield the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6): 5.90 (m, 1H); 4.71 (bs, 2H); 4.58 (bs, 2H); 3.67 (s, 3H); 1.42 (s, 9H). MS (m/z) ES+: 171 (10; MH+ minus tert-butyl); 57 (100).

Workup

  1. temperaturerefluxed for 2.5 hours
  2. waitleft over night at room temperature
  3. filtrationThe precipitate is filtered off
  4. washwashed with TBME
  5. customthe filtrate purified via chromatography (TBME/hexane 2:8>3:7)

Sources & evidence

ORD record
ord-10c613c2f30549a79f09f1435e1b9d38
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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