Potassium Bromide → N-butyl-2-((4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

HRID 877945Notes

Reaction equation

HRID 877945 reaction equation
[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH2:14][OH:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH3:4].CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+]>C(Cl)Cl>[CH2:1]([NH:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:13][C@@H:12]([CH:14]=[O:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 253877Potassium BromideHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 53339170N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Product 1

HCID 24826227N-butyl-2-((4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl) acetamide (6 grams) in methylene chloride (24 ml) was added to a pre-cooled mixture of TEMPO (0.01 gram), methylene chloride (36 ml) and potassium bromide (0.26 grams) at −5 to −15° C. Sodium hypo chlorite (15.6 ml) was added to the reaction mixture at −15 to −5° C. and stirred. After completion of the reaction, quenched it with 10% sodium thio sulfate solution at room temperature and water was added to it. Both organic and aqueous layers were separated and organic layer was washed with water followed by saturated sodium chloride solution. The solvent from organic layer was distilled off under reduced pressure to get the title compound.

Workup

  1. customAfter completion of the reaction
  2. customquenched it with 10% sodium thio sulfate solution at room temperature
  3. additionwater was added to it
  4. customBoth organic and aqueous layers were separated
  5. washorganic layer was washed with water
  6. distillationThe solvent from organic layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0ba0adec03ac4a669bd0b4953a7f5230
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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