2-Amino-1-(3-chlorophenyl)ethan-1-ol → 4-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione, hemihydrate

HRID 465415Notes

Reaction equation

HRID 465415 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:11])[CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.[Na].[CH2:13]([C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[C:23]=2[OH:29])=[CH:19][CH:18]=1)[C:14]([CH3:16])=O.C([BH3-])#N.[Na+]>C(O)C>[OH2:11].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]([OH:11])[CH2:9][NH:10][CH:14]([CH3:16])[CH2:13][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[C:23]=2[OH:29])=[CH:19][CH:18]=1.[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]([OH:11])[CH2:9][NH:10][CH:14]([CH3:16])[CH2:13][C:17]1[CH:31]=[CH:30][C:20]([O:21][C:22]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[C:23]=2[OH:29])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 547233674-(4-acetonylphenoxy)-3-hydroxy-1H-pyrrole-2,5-dione

Product 1

HCID 1317175664-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione, hemihydrateYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(3-chlorophenyl)-2-hydroxyethylamine (0.6 g) and the sodium salt of 4-[4-acetonylphenoxy]-3-hydroxy-1H-pyrrole-2,5-dione(1.0 g) in ethanol, was treated with sodium cyanoborohydride (0.25 g) and stirred at ambient temperature for 18 h. The solvent was evaporated in vacuo, the residue shaken with ethyl acetate and water and filtered. The insoluble material was washed with acetone and crystallised from methanol: water (95:5) to give 4-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxy]-3-hydroxy-1H-pyrrole-2,5-dione, hemihydrate, (0.55 g), as a (27:73)mixture of diastereoisomers.

Workup

  1. customThe solvent was evaporated in vacuo
  2. stirringthe residue shaken with ethyl acetate and water
  3. filtrationfiltered
  4. washThe insoluble material was washed with acetone
  5. customcrystallised from methanol: water (95:5)

Sources & evidence

ORD record
ord-fe497ae9375044aa9c74ceef2f3aef23
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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