(R*,R*)-N-[5-[1-Hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]formamide → (R,R)-Formoterol

HRID 572705Notes

Reaction equation

HRID 572705 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([CH:13]([OH:34])[CH2:14][N:15](CC2C=CC=CC=2)[CH:16]([CH3:26])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:10]=1[NH:37][CH:38]=[O:39])C1C=CC=CC=1.[H][H]>[Pd]>[CH3:26][C@@H:16]([NH:15][CH2:14][C@H:13]([OH:34])[C:12]1[CH:35]=[CH:36][C:9]([OH:8])=[C:10]([NH:37][CH:38]=[O:39])[CH:11]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 11734094(R*,R*)-N-[5-[1-Hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]formamideHCID 178418361HCID 178418361, compound

Product 1

HCID 3083544(R,R)-Formoterol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-benzyloxy-3-formylamino-α-[N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)aminomethyl]benzyl alcohol (120 gms, 0.23 M), 10% Pd/C (12 gms) and denatured spirit (0.6 lit) were introduced in an autoclave. The reaction mass was hydrogenated by applying 4 kg hydrogen pressure at 25-30° C. for 3 hrs. The catalyst was removed by filtration and the clear filtrate concentrated under reduced pressure below 40° C. to yield the title compound. (63 gms, 80%).

Workup

  1. additionwere introduced in an autoclave
  2. customat 25-30° C.
  3. customfor 3 hrs
  4. customThe catalyst was removed by filtration
  5. concentrationthe clear filtrate concentrated under reduced pressure below 40° C.

Sources & evidence

ORD record
ord-89484407c8134df6a6dcbb1da1b947c2
Source dataset
uspto-grants-2015_05
Patent number
US09029421B2

Reaction notes

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