(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpent-4-yn-3-ol → (2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpentan-3-ol

HRID 1856693Notes

Reaction equation

HRID 1856693 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@H:7]([CH:9]([OH:18])[C:10]#[C:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:8])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Rh]>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@H:7]([CH:9]([OH:18])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:8])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 57103943(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpent-4-yn-3-ol

Product 1

HCID 57000220(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpentan-3-ol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpent-4-yn-3-ol (5.93 g, Example 15c)) was dissolved in ethyl acetate (100 ml) and hydrogenated at 5 atmospheres using 5% rhodium on charcoal (2.0 g) as catalyst. The mixture was filtered through Celite® and the filtrate concentrated under reduced pressure to give the sub-title compound as an oil and as a 4:1 mixture of diastereomers (5.6 g). The diastereomers were separated using normal-phase HPLC eluting with 3% isopropyl alcohol in dichloromethane to give (2S,3R)-2-(4-bromophenoxy)-5-(pyridin-3-yl)-3-pentanol as the major diastereomer (3.21 g) and (2S,3S)-2-(4-bromophenoxy)-5-(pyridin-3-yl)-3-pentanol as the minor diastereomer (0.71 g).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-571489c0726745f9bf96c024959435a9
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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