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

HRID 1025237Notes

Reaction equation

HRID 1025237 reaction equation
[CH3:1][NH:2][CH3:3].C([N:8]([CH:16]1[CH2:18][CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C#C.[CH2:19]1C[O:22][CH2:21][CH2:20]1>>[CH3:1][N:2]([CH3:3])/[CH:19]=[CH:20]/[C:21]([C:16]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:17][CH2:18]1)=[O:22]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 86658615Tert-butyl propioloylcyclopropylcarbamate

Product 1

HCID 67291958(E)-tert-butyl 1-(3-(dimethylamino)acryloyl)cyclopropylcarbamate

Procedure

A 2M solution of dimethylamine in THF (14.5 ml) and tert-butyl propioloylcyclopropylcarbamate (1.5 g, 7.17 mmol, 1.0 eq) was stirred at 0° C., and then the stirring continued at r.t. for 4 hr. TLC showed completion of the reaction. The reaction mixture was concentrated to yield the crude solid product which was then recrystalised in EtOAC/Pet ether to get the desired product as light yellow solid. Yield: 1.4 g (77.8%). 1H NMR (400 MHz, CDCl3): δ7.59 (d, J=12.4, 1H), 5.52 (d, J=10.8, 1H), 5.37 (d, J=12.4, 1H), 3.07 (bs, 3H), 2.82 (bs, 3H), 1.52 (s, 2H), 1.45 (s, 9H), 1.05 (s, 2H). LCMS: (ES+) m/z=255.2 (M+H)+

Workup

  1. customcompletion of the reaction
  2. concentrationThe reaction mixture was concentrated
  3. customto yield the crude solid product which
  4. customwas then recrystalised in EtOAC/Pet ether

Sources & evidence

ORD record
ord-5da209b5f6794cc691f7bb82d2461dfb
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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