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

HRID 877944Notes

Reaction equation

HRID 877944 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[OH:6][CH2:7][C@H:8]1[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@@H:10]([CH2:16][C:17](OC)=[O:18])[CH2:9]1>>[CH2:1]([NH:5][C:17](=[O:18])[CH2:16][C@H:10]1[CH2:9][C@@H:8]([CH2:7][OH:6])[O:13][C:12]([CH3:14])([CH3:15])[O:11]1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 8007ButylamineHCID 10560752methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Product 1

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

Procedure

Mixture of n-butyl amine (100 grams), methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (20 grams) was heated to reflux and stirred. After completion of the reaction, distilled off n-butylamine under reduced pressure at below 60° C. The obtained residue was further purified using mixture of cyclohexane and ethyl acetate.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customAfter completion of the reaction
  4. distillationdistilled off n-butylamine under reduced pressure at below 60° C
  5. customThe obtained residue was further purified
  6. additionmixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-c26ec31d65c3469187fb99e824e69962
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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