(S)-1-[P-(Benzyloxy)phenoxy]-3-(isopropylamino)propan-2-OL → Prenalterol

HRID 2417992Notes

Reaction equation

HRID 2417992 reaction equation
C([O:8][C:9]1[CH:23]=[CH:22][C:12]([O:13][CH2:14][C@@H:15]([OH:21])[CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:23]=[CH:22][C:12]([O:13][CH2:14][C@@H:15]([OH:21])[CH2:16][NH:17][CH:18]([CH3:19])[CH3:20])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 12941036(S)-1-[P-(Benzyloxy)phenoxy]-3-(isopropylamino)propan-2-OL

Product 1

HCID 42396PrenalterolYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-1-(4-benzyloxyphenoxy)-3-(1-methylethyl)amino-2-propanol (53.4 g) in 500 ml methanol was hydrogenated over 5 g 10% palladium on carbon (room temperature; 1 atmosphere). Within 40 minutes the uptake of nitrogen stopped abruptly after the absorption of 4,300 ml. The mixture was filtered through Celite and the filtrate was concentrated to dryness under reduced pressure. The resulting colorless solid residue was crystallized from acetone to give 35.2 g of (S)-1-(4-hydroxyphenoxy)-3-(1-methylethyl)amino-2-propanol, mp 127°-129°; [α]D25 -20.67° (c, 1.0, 0.1N hydrochloric acid).

Workup

  1. customafter the absorption of 4,300 ml
  2. filtrationThe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. customThe resulting colorless solid residue was crystallized from acetone

Sources & evidence

ORD record
ord-841f4fb890d2485d845cce1bbcc3b79c
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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