1-Aminocyclopropane-1-carboxylic acid → 5-(3-Methoxy-2-methylphenyl)-6-oxa-4-azaspiro[2.4]hept-4-en-7-one

HRID 1091235Notes

Reaction equation

HRID 1091235 reaction equation
[NH2:1][C:2]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3]1.[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=O>N1C=CC=CC=1.CCOCC>[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([C:13]2[O:6][C:5](=[O:7])[C:2]3([CH2:4][CH2:3]3)[N:1]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 14719554Benzoyl chloride, 3-methoxy-2-methyl-

Product 1

HCID 597133875-(3-Methoxy-2-methylphenyl)-6-oxa-4-azaspiro[2.4]hept-4-en-7-oneYield 78.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1-aminocyclopropanecarboxylic acid (1.06 g, 10.5 mmol) in pyridine (20 mL) cooled to ˜5° C., solid 3-methoxy-2-methylbenzoyl chloride (4.35 g, 23.6 mmol) was added. The mixture was stirred at room temperature for 1 week and evaporated under reduced pressure to leave an oily solid. This material was taken up in 20% ether in hexanes (175 mL), washed with water (50 mL), 5% aqueous HCl (2×50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was dried over MgSO4 and evaporated under reduced pressure to leave 5-(3-methoxy-2-methyl-phenyl)-6-oxa-4-aza-spiro[2.4]hept-4-en-7-one (1.90 g) as a yellow solid. 1H NMR (CDCl3) δ (ppm): 1.80 (m, 2H), 1.90 (m, 2H), 2.49 (s, 3H), 3.85 (s, 3H), 7.01 (d, 1H), 7.22 (t, 1H), 7.40 (d, 1H).

Workup

  1. customevaporated under reduced pressure
  2. customto leave an oily solid
  3. washwashed with water (50 mL), 5% aqueous HCl (2×50 mL) and saturated aqueous NaHCO3 (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-09c748aa03c44f4fbd12e6af789a1809
Source dataset
uspto-grants-2012_03
Patent number
US08129355B2

Reaction notes

Loading…