Methyl Acrylate → HCID 67071461, compound

HRID 874223Notes

Reaction equation

HRID 874223 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18](Br)[CH:19]=3)[O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:30][O:29][C:25](=[O:28])/[CH:26]=[CH:27]/[C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[O:14][C:10]1([CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)[CH2:22][C:21]2=[O:23]

Participants

6

Reactant 2

HCID 7294Methyl AcrylateHCID 58424126HCID 58424126, compound

Product 1

HCID 67071461HCID 67071461, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (±)-6-bromo-4-oxo-spiro(chromane-2,3′-piperidine)-1′-carboxylic acid tert-butyl ester (6.0 g, 15.19 mmol), Pd(OAc)2 (68.1 mg, 0.304 mmol), P(o-tol)3 (184.7 mg, 0.608 mmol), TEA (6.33 ml, 45.6 mmol), methyl acrylate (4.10 ml, 45.57 mmol) in dry DMF (15 ml) was heated under N2 atmosphere to 100° C. for 3 h. After cooling down to RT, the solution was filtered on a celite pad and washed 3 times with EtOAc (100 ml). The filtrate was washed with water and brine. The organic phase was dried over Na2SO4 and evaporated under vacuum. The crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 8:2 to 7:3) to give (±)-(E)-3-[1′-tert-butoxycarbonyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (6.0 g) as a yellow solid.

Workup

  1. temperatureAfter cooling down to RT
  2. filtrationthe solution was filtered on a celite pad
  3. washwashed 3 times with EtOAc (100 ml)
  4. washThe filtrate was washed with water and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated under vacuum
  7. customThe crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 8:2 to 7:3)

Sources & evidence

ORD record
ord-ce6eed5aeab54b13b815b0d4056d6e09
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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