Formaldehyde → 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester

HRID 1789839Notes

Reaction equation

HRID 1789839 reaction equation
C(NCC)C.[CH2:6]([O:8][C:9](=[O:37])[CH:10]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:19][C:20]=1[CH3:21])[C:11](O)=O)[CH3:7].C=O.C(OCC)(=O)C>C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:37])[C:10]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])=[CH:19][C:20]=1[CH3:21])=[CH2:11])[CH3:7]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 536521632-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester

Product 1

HCID 539435542-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylamine (0.26 g, 2.67 mmol) was added a mixture of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.0 g, 2.2 mmol) and 37% aq. solution of formaldehyde (0.24 g, 3.00 mmol) in methylene chloride (2 mL) at 0° C. The mixture was stirred for 16 h at room temperature and ethyl acetate was added. The organic layer was washed with water and 5% NaHCO3 and dried. Concentration under reduced pressure followed by flash chromatography (toluene/ethyl acetate, 3:1→1:1) gave 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.81 g, 88%).

Workup

  1. washThe organic layer was washed with water and 5% NaHCO3
  2. customdried
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-bfa4f575661a4f058260736ab655e8f3
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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