Dimethylamine → (E)-tert-butyl 1-(3-(dimethylamino)acryloyl)cyclopropylcarbamate

HRID 1040483Notes

Reaction equation

HRID 1040483 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1([C:11](=[O:14])[C:12]#[CH:13])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH:16]([CH3:18])[CH3:17]>>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1([C:11](=[O:14])/[CH:12]=[CH:13]/[N:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 86646201Tert-butyl N-[1-(prop-2-ynoyl)cyclopropyl]carbamate

Product 1

HCID 67291958(E)-tert-butyl 1-(3-(dimethylamino)acryloyl)cyclopropylcarbamateYield 67.4%

Procedure

(1-Propynoyl-cyclopropyl)-carbamic acid tert-butyl ester (2.2 g, 10.5 mmol) was dissolved in a solution of Me2NH (2 M in THF, 21 mL, 42 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 h and then the volatiles were removed in vacuo to give a crude solid. The solid was purified by washing with n-pentane and Et2O to give 1.8 g of the title compound as a yellow solid, m/z 255.36 [M+1]+.

Workup

  1. customthe volatiles were removed in vacuo
  2. customto give a crude solid
  3. customThe solid was purified
  4. washby washing with n-pentane and Et2O

Sources & evidence

ORD record
ord-617cddb9aa8b47cba00522cd85b1f9a4
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…