HCID 67831543, compound → HCID 67830872, compound

HRID 1708879Notes

Reaction equation

HRID 1708879 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([CH:15]([O:18][CH3:19])[O:16][CH3:17])[N:12]1CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH3:12].[CH3:17][O:16][CH:15]([O:18][CH3:19])[C@H:13]1[NH:12][C@@H:11]([C:9]([OH:10])=[O:8])[CH2:14]1

Participants

6

Reactant 2

HCID 67831543HCID 67831543, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 222AmmoniaHCID 67830872HCID 67830872, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

12.5 mg (35 μmol) of cis-N-benzYl-4-(dimethoxymethyl)azetidine-2-carboxylic acid benzyl ester in 10 ml of methanol is hydrogenated in a Parr shaker over 53 mg of 20% Pd(OH)2/C (containing 31% water) under 4 atm of hydrogen for 3 h. Filtration through a double paper filter, repeated washing with methanol and evaporation gives a crude product which is filtered over silica gel with isopropanol/water/conc. ammonia (17:2:1) to yield 3.0 mg (49%) of cis-4(dimethoxymethyl)azetidine-2-carboxylic acid as a colorless glass. 1H NMR (D2O): δ4.73 (d, 1H, overlapping), 4.72 (t, 1H, overlapping), 3.53 (s, 3H), 3.50 (s, 3H), 2.80 (dt, 1H, J=12 (d), 9.5(t)), 2.50 (dt, 1H, J=12(d), 8(t)).

Workup

  1. filtrationFiltration through a double paper
  2. filtrationfilter
  3. washrepeated washing with methanol and evaporation
  4. customgives a crude product which
  5. filtrationis filtered over silica gel with isopropanol/water/conc

Sources & evidence

ORD record
ord-50f5b6808a2f40c4ab5f210b11c084bb
Source dataset
uspto-grants-1990_08
Patent number
US04946839

Reaction notes

Loading…