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

HRID 877950Notes

Reaction equation

HRID 877950 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 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

Sources & evidence

ORD record
ord-b273afee20fe4c5db7c346d0d7b47bfd
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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