Butylamine → N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

HRID 877952Notes

Reaction equation

HRID 877952 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]([O:14]C(C)(C)C)=O)[CH2:4]1.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:19]([NH:23][C:12](=[O:14])[CH2:11][C@H:5]1[CH2:4][C@@H:3]([CH2:2][OH:1])[O:8][C:7]([CH3:9])([CH3:10])[O:6]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Product 1

HCID 53339170N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
42.5 °C

Procedure

A mixture of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (10 grams), methanol (80 ml), n-butyl amine (20 ml) and potassium carbonate (10.6 grams) was heated to 40-45° C. and stirred up to completion of the reaction. The reaction mixture was distilled under reduced pressure and methylene chloride (100 ml) was added to the obtained residue at 25-30° C. and stirred for 15 minutes. The unwanted solid was filtered off and the filtrate was distilled off under reduced pressure. The obtained residue was dissolved in methylene chloride (32 ml) and a mixture of TEMPO (0.015 grams), potassium bromide (0.36 grams) in methylene chloride (48 ml) was added to it and stirred for 15 minutes. Sodium hypochlorite solution (20.8 ml) was added to the reaction mixture at −15 to 15° C. and stirred for an hour. After completion of the reaction, the reaction mixture was quenched with sodium thio sulfate solution at below 10° C. Both organic and aqueous layers were separated and aqueous layer extracted with methylene chloride. The solvent from organic layer was distilled off under reduced pressure to get the title compound.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure and methylene chloride (100 ml)
  2. additionwas added to the obtained residue at 25-30° C.
  3. stirringstirred for 15 minutes
  4. filtrationThe unwanted solid was filtered off
  5. distillationthe filtrate was distilled off under reduced pressure
  6. dissolutionThe obtained residue was dissolved in methylene chloride (32 ml)
  7. additiona mixture of TEMPO (0.015 grams), potassium bromide (0.36 grams) in methylene chloride (48 ml)
  8. additionwas added to it
  9. stirringstirred for 15 minutes
  10. additionSodium hypochlorite solution (20.8 ml) was added to the reaction mixture at −15 to 15° C.
  11. stirringstirred for an hour
  12. customAfter completion of the reaction
  13. customthe reaction mixture was quenched with sodium thio sulfate solution at below 10° C
  14. customBoth organic and aqueous layers were separated
  15. extractionaqueous layer extracted with methylene chloride
  16. distillationThe solvent from organic layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d78eea3f3e6a4943a8cd5c0a573f2e1a
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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