Dichloromethane → 2-[(4R,6S)-6-formyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide

HRID 445934Notes

Reaction equation

HRID 445934 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH2:4]1.ClCCl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O>[CH:2]([C@H:3]1[O:8][C:7]([CH3:9])([CH3:10])[O:6][C@@H:5]([CH2:11][C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 866815062-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide

Product 1

HCID 866815072-[(4R,6S)-6-formyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamideYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (5.0 g), dichloromethane (30.0 mL), and Dess-Martin periodinane (11.2 g) were added to a reactor under nitrogen atmosphere. The reaction mixture was stirred at 20˜30° C. for over 5 hours. Water (30.0 mL) was added to the reaction mixture. The separated organic layer was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1:3) to obtain 2-[(4R,6S)-6-formyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide as a white solid (4.3 g, yield 87%).

Workup

  1. concentrationThe separated organic layer was concentrated under reduced pressure
  2. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1:3)

Sources & evidence

ORD record
ord-1cfd47905d68479f8575d36e3b2f4053
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Reaction notes

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