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

HRID 445935Notes

Reaction equation

HRID 445935 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.C(=O)(O)[O-].[Na+].[Br-].[K+].Cl[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC1(C)N([O])C(C)(C)CCC1.C(OCC)(=O)C>[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

8

Reactant 5

HCID 24437Sodium SulfiteHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 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 93.1%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (30.0 g), ethyl acetate (240.0 mL), sodium bicarbonate (28.5 g), potassium bromide (3.0 g), and TEMPO (0.06 g) were added to a reactor. The temperature of the reaction mixture was adjusted to 0˜5° C. 10% Sodium hypochlorite solution (96.0 mL) was slowly added to the reaction mixture, which was then stirred at 0˜5° C. for 2 hours. 5% Sodium sulfite solution (150.0 mL) was added to the reaction mixture. The separated organic layer was washed with 10% sodium chloride solution (150.0 mL). The organic layer was concentrated under reduced pressure to obtain 2-[(4R,6S)-6-formyl-2,2-dimethyl-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide as a light brown solid (27.7 g, yield 93%).

Workup

  1. customwas adjusted to 0˜5° C
  2. washThe separated organic layer was washed with 10% sodium chloride solution (150.0 mL)
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9b4e6af9a5f4c69b078551ec7c54cf2
Source dataset
uspto-grants-2013_07
Patent number
US08476432B2

Reaction notes

Loading…