Water → HCID 14654427, compound

HRID 981039Notes

Reaction equation

HRID 981039 reaction equation
C([O:8][C:9]([CH:11]1[CH2:14][CH:13]([CH2:15][OH:16])[N:12]1CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1.O.[H][H]>CO.[OH-].[OH-].[Pd+2]>[OH:16][CH2:15][CH:13]1[NH:12][CH:11]([C:9]([OH:10])=[O:8])[CH2:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 14654423HCID 14654423, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14654427HCID 14654427, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

179 mg (0.575 mmol) of N-benzyl-4-(hydroxymethyl)azetidine-2-carboxylic acid benzyl ester and 60 mg of 20% Pd(OH)2 /C (containing 31% of water) in 30 ml of methanol are hydrogenated in a Parr shaker under 4 atm of hydrogen for 3.5 h. The catalyst is filtered off through a double paper filter and washed with methanol, the solution evaporated, and the residue chromatographed on silica gel (isopropanol/water/conc. NH3 14:5:1) to yield, after evaporation and drying i.v., 53.6 mg (71%) of 4-(hydroxymethyl)azetidine-2-carboxylic acid as a colorless solid. 1H NMR (D2O): δ 4.71 (t, 1H, J=9), 4.56 (m, 1H), 3.80 (m, 2H), 2.81 (dt, 1H, J=12 (d), 9.5 (t)), 2.43 (dt, 1H, J=12.5 (d), 8.5 (t)). IR (nujol): 3239, 3146, 2589, 2438, 1620, 1565, 1410, 1327, 1302, 1188, 1099, 1038, 999, 885, 828, 758, 725 cm-1.

Workup

  1. filtrationThe catalyst is filtered off through a double paper
  2. filtrationfilter
  3. washwashed with methanol
  4. customthe solution evaporated
  5. customthe residue chromatographed on silica gel (isopropanol/water/conc. NH3 14:5:1)
  6. customto yield
  7. customafter evaporation
  8. customdrying i.v

Sources & evidence

ORD record
ord-42b49f35f7534b7dbfbbf648e5f7202a
Source dataset
uspto-grants-1991_02
Patent number
US04990504

Reaction notes

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