(3Rs,4r)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol → (3s,4r)-4-(4-Bromophenoxy)-1-pyridin-3-yl-pentan-3-ol

HRID 379977Notes

Reaction equation

HRID 379977 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@H:7]([CH3:18])[CH:8]([OH:17])[C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Rh]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@H:7]([CH3:18])[C@@H:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 53929738(3Rs,4r)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol

Product 1

HCID 57244445(3s,4r)-4-(4-Bromophenoxy)-1-pyridin-3-yl-pentan-3-ol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the method described in Example 1d) from (3RS,4R)-4-(4-bromophenoxy)-1-pyridin-3-yl-pent-1-yn-3-ol (5.93 g, Example 4c)) and 5% rhodium on charcoal (2.0 g) in ethyl acetate (100 ml) 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-pentan-3-ol as the majordiastereomer (3.21 g) and (2S, 3S)-2-(4-bromophenoxy)-5-pyridin-3-yl-pentan-3-ol as the second eluting and minor diastereomer (0.71 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b91b1b2a02cc4e6cb3c01fa5dac6b7ff
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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