HCID 58100156, compound → HCID 58100069, compound

HRID 1696857Notes

Reaction equation

HRID 1696857 reaction equation
[Cr](Cl)([O-])(=O)=O.[OH:6][CH:7]([CH3:32])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:13][CH:12]=1>ClCCl>[O:6]=[C:7]([CH3:32])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 58100156HCID 58100156, compoundHCID 178418299HCID 178418299, compound

Product 1

HCID 58100069HCID 58100069, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyrididium chlorochromate (7.32 g, 34.00 mmol) was added to a mixture of benzyl 4-[4-(4-hydroxypentyl)phenyl]butylcarbamate (138) (6.27 g, 17.00 mmol) and 4 Å molecular sieves in dichloromethane (250 mL) in three portions and stirred at rt for 6 h. The reaction mixture was then filtered through diatomaceous earth and the filtrate was concentrated to a black oil. Purification by column chromatography (silica, 30:70 ethyl acetate/hexanes) afforded ketone 140 (6.58 g, >99% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.50-1.56 (m, 2H), 1.60-1.66 (m, 2H), 1.85-1.90 (m, 2H), 2.11 (s, 3H), 2.42 (t, 2H), 2.56-2.60 (m, 4H), 3.19-3.23 (m, 2H), 4.70 (br s, 1H), 5.08 (s, 2H), 7.07 (s, 4H), 7.29-7.36 (m, 5H).

Workup

  1. filtrationThe reaction mixture was then filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated to a black oil
  3. customPurification by column chromatography (silica, 30:70 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-160d71d48c63467bbc61d767be464983
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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