HCID 53873774, compound → HCID 22005141, compound

HRID 324868Notes

Reaction equation

HRID 324868 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]([CH:26]=[CH:27][CH2:28][CH2:29][CH3:30])=[C:6]([CH:31]([CH3:33])[CH3:32])[N:5]=1)([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH:1]([C:4]1[C:9]([CH:10]=[O:11])=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:7]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[C:6]([CH:31]([CH3:32])[CH3:33])[N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 53873774HCID 53873774, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22005141HCID 22005141, compoundYield 84.3%

Procedure

2,6-Diisopropyl-3-hydroxymethyl-4-(2-benzyloxyphenyl)-5-(pent-1-enyl)-pyridine (Example 162) (680 mg, 1.53 mmol) was dissolved in 15 mL of methylene 25 chloride under an argon atmosphere and treated with a mixture of Celite (661 mg) and pyridinium chlorochromate (“PCC”) (661 mg, 2 eq). The reaction was stirred at room temperature for 1.5 h. The suspension was filtered through a pad of silica and the pad was washed with 50 mL CH2Cl2 and the filtrate was combined and concentrated in vacuo to afford 572.4 mg of product (84%). 1H NMR (300 MHz, CDCl3): δ 0.70 (t, J=7.2 Hz, 3 H), 1.08-1.35 (m, 61 H), 4.9-1.93 (m, 1 H), 3.26-3.45 (m, 1 H), 3.87-3.97 (m, 1 H), 4.97-5.06 (m, 2 H), 5.27-5.50 (m, 1 H), 6.01-6.10 (m, 1 H), 6.94-7.34 (m, 9 H), 9.82 (d, J=3.6 Hz, 1 H).

Workup

  1. filtrationThe suspension was filtered through a pad of silica
  2. washthe pad was washed with 50 mL CH2Cl2
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efb7ff0bdaf04c69b6807a7a14d26f2a
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

Loading…