(3RS, 4S)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hex-1-yn-3-ol → (3r,4s)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hexan-3-ol

HRID 380051Notes

Reaction equation

HRID 380051 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@@H:7]([CH2:18][CH3:19])[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]([CH2:18][CH3:19])[C@H:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 70246681(3RS, 4S)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hex-1-yn-3-ol

Product 1

HCID 57271083(3r,4s)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hexan-3-ol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the method described in Example 1d) from (3RS,4S)-4-(4-bromophenoxy)-1-pyridin-3-yl-hex-1-yn-3-ol (3.42 g, Example 87c)) and 5% rhodium on carbon (0.5 g) in ethyl acetate (100 ml). After work up crude material was purified by flash column chromatography over silica eluting with ethyl acetate to give a mixture of diastereomers. The mixture was separated by normal-phase HPLC eluting with 2% propan-2-ol in dichloromethane to give the sub-title compound as the second eluting, major diastereomer (2 g).

Workup

  1. customPrepared
  2. customAfter work up crude material was purified by flash column chromatography over silica eluting with ethyl acetate
  3. customto give
  4. additiona mixture of diastereomers
  5. customThe mixture was separated by normal-phase
  6. washHPLC eluting with 2% propan-2-ol in dichloromethane

Sources & evidence

ORD record
ord-98e84a6d5bc44573b6015a2d2ac36025
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

Loading…