Water → HCID 14654420, compound

HRID 1708873Notes

Reaction equation

HRID 1708873 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([C:15](=[O:17])[NH2:16])[N:12]1CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1.O>CO.[Pd]>[C:15]([C@H:13]1[NH:12][C@@H:11]([C:9]([OH:10])=[O:8])[CH2:14]1)(=[O:17])[NH2:16]

Participants

5

Reactant 2

HCID 962WaterHCID 14654415HCID 14654415, compound

Product 1

HCID 14654420HCID 14654420, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

53 mg (163 umol) of cis-1-benzyl-4-carbamoylazetidine-2-carboxylic acid benzyl ester (II) in 10 ml of methanol are hydrogenated in a Parr shaker over 18 mg of 10% Pd/C under a hydrogen pressure of 3.3 atm for 3 hours. 10 ml of water is added, the mixture filtered through a fluted filter, and the catalyst washed with several portions of methanol. Evaporation and drying in vacuo (0.1 torr, 4 hours) affords 22.6 mg (96%) of a colorless glass. 1H NMR (D2O): δ 5.00 (t, 1H, J=9), 4.75 (t, 1H, J=9), 3.14 (dt, 1H, J=10 (t), 12 (d)), 2.52 (dt, 1H, J=8(t), 12 (d)). IR (nujol): 3399, 3141, 3141, 3019, 2537, 2409, 1688, 1615, 1563, 1391, 1294, 1217, 1165, 1115, 1048, 968, 887, 810, 762, 696, 637 cm-1. Mass Spectra: El: m/z 142(M-2H, 40%), 100 (100), 91 (14), 82 (27), 68 (28), 54 (50), 44 (95); CI (isobutane): m/z 145 (M+ H, 100%), 126 (7), 100 (24), 99 (15), 84 (15), 72 (22).

Workup

  1. customfor 3 hours
  2. filtrationthe mixture filtered through
  3. filtrationa fluted filter
  4. washthe catalyst washed with several portions of methanol
  5. customEvaporation
  6. customdrying in vacuo (0.1 torr, 4 hours)

Sources & evidence

ORD record
ord-a0eba31dc7964bc994e77ab737419600
Source dataset
uspto-grants-1990_08
Patent number
US04946839

Reaction notes

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