(3s, 4s)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol → (3RS, 4S)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol

HRID 380021Notes

Reaction equation

HRID 380021 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C@@H:7]([CH:18]([CH3:20])[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.BrC1C=CC(O[C@@H](C(C)C)[C@@H](O)CCC2C=NC=CC=2)=CC=1.BrC1C=CC(O[C@@H](C(C)C)[C@H](O)CCC2C=NC=CC=2)=CC=1>C(OCC)(=O)C.[Rh]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]([CH:18]([CH3:19])[CH3:20])[CH:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 57006887(3s, 4s)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanolHCID 57267460(3S,4R)-3-(4-bromophenyloxy)-2-methyl-6-(3-pyridyl)hexan-4-olHCID 131722885(3RS, 4S)-4-(4-Bromophenoxy)-5-(methyl)-1-(pyridin-3-yl)-hex-1-yn-3-ol

Product 1

HCID 131722886(3RS, 4S)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3RS, 4S)-4-(4-Bromophenoxy)-5-(methyl)-1-pyridin-3-yl-hex-1-yn-3-ol (13.6 g) was dissolved in ethyl acetate (350 ml) and hydrogenated at 3 atmospheres for 6 days using 10% rhodium on charcoal (2.1 g) as catalyst. The catalyst and solvent were replaced 5 times during this period. The mixture was filtered through Celite® and the filtrate concentrated under reduced pressure to give a. The mixture was purified by HPLC eluting with dichoromethane:2-propanol (97:3) to give a mixed fraction containing reduced and unreduced (6.0 g), pure (3S, 4S)-4-(4-bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol (1.73 g) and pure (3R,4S)-4-(4-bromophenoxy)-5-(methyl)-1-pyridin-3-yl-3-hexanol (2.73 g).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give a
  4. customThe mixture was purified by HPLC
  5. washeluting with dichoromethane:2-propanol (97:3)
  6. customto give a mixed fraction
  7. additioncontaining

Sources & evidence

ORD record
ord-c656b59b20564a4dba1d8c2e24763d08
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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