HCID 10363976, compound → HCID 53714199, compound

HRID 1462378Notes

Reaction equation

HRID 1462378 reaction equation
C([N:8]([CH2:22][C@H:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19](=[O:21])[NH2:20])[CH:13]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:19]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[OH:18])[O:11][CH2:10][CH2:9][NH:8][CH2:22][C@H:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:21])[NH2:20]

Participants

5

Reactant 2

HCID 10363976HCID 10363976, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53714199HCID 53714199, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 23 g of crude (R)-α-[N-benzyl-N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol in 230 ml of methanol is hydrogenated, with the addition of 5 g of palladium-charcoal catalyst (5%), under normal conditions until 1 mol-equivalent of hydrogen has been absorbed. The catalyst is subsequently filtered off, is washed with methanol, and the combined methanolic solutions are concentrated under reduced pressure. The crystalline residue is recrystallised from methanol and yields (R)-(-)-α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol, m.p. 166°-172°; [α]D =-23°±1° (C=0.6% in methanol).

Workup

  1. customhas been absorbed
  2. filtrationThe catalyst is subsequently filtered off
  3. washis washed with methanol
  4. concentrationthe combined methanolic solutions are concentrated under reduced pressure
  5. customThe crystalline residue is recrystallised from methanol

Sources & evidence

ORD record
ord-3e1dfbc7c0664858bd04c00092f28cb8
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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