Triacetoxyperiodinane → HCID 55269063, compound

HRID 1776186Notes

Reaction equation

HRID 1776186 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][S:24]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH2:32][OH:33])(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH:32]=[O:33])(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 20696594HCID 20696594, compound

Product 1

HCID 55269063HCID 55269063, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.7 g, 4 mmol) was added to a solution of (1-(methylsulfonyl)pyrrolidin-2-yl)methanol (0.570 g, 3.18 mmol) in anhydrous methylene chloride (20 mL). The reaction was stirred for 24 hours and a second portion of Dess-Martin periodinane (1 g, 2.3 mmol) was added. The resulting suspension was stirred for 24 hours, filtered, and concentrated. The crude residue was purified by silica gel column chromatography (1-15% ethyl acetate in methylene chloride) to provide a white waxy solid (0.44 g, 78%). 1H NMR (CDCl3, 300 MHz) δ 9.58 (d, 1H, J=1.2 Hz), 4.25-4.20 (td, 1H, J=6.9, 1.2 Hz), 3.55-3.44 (m, 2H), 2.97 (s, 3H), 2.21-2.13 (m, 2H), 2.05-1.90 (m, 2H).

Workup

  1. stirringThe resulting suspension was stirred for 24 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude residue was purified by silica gel column chromatography (1-15% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-9e10dfea501b4dbf8130bd32e62c62da
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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