Triacetoxyperiodinane → HCID 63845011, compound

HRID 1776190Notes

Reaction equation

HRID 1776190 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][S:24]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[CH2:33][OH:34])(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[CH:33]=[O:34])(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 33302341-(Methylsulfonyl)-2-piperidinemethanol

Product 1

HCID 63845011HCID 63845011, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (21 g, 50 mmol) was added to a solution of (1-(methylsulfonyl)piperidin-2-yl)methanol (4.9 g, 25.4 mmol) in anhydrous methylene chloride (125 mL). The reaction was stirred for 24 hours, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (25-75% ethyl acetate in hexanes) to provide a white waxy solid (1.1 g, 24% yield). 1H NMR (CDCl3, 300 MHz) δ 9.56 (s, 1H), 4.61-4.58 (br d, 1H, J=6.3 Hz), 3.75-3.68 (m, 1H), 3.13-3.04 (td, 1H, J=12.0, 3.2 Hz), 2.97 (s, 3H), 2.33-2.22 (m, 1H), 1.89-1.55 (m, 4H), 1.27-1.21 (m, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by silica gel column chromatography (25-75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f1faf2377e444d02aecbbc6369b7939c
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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