Acetonitrile → 1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanone
Reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.Br[CH2:12][C:13]([C:15]1[CH:26]=[CH:25][C:18]2[O:19][C:20]([CH3:24])([CH3:23])[O:21][CH2:22][C:17]=2[CH:16]=1)=[O:14].C(N(CC)C(C)C)(C)C.C(#N)C>C1COCC1>[CH3:23][C:20]1([CH3:24])[O:19][C:18]2[CH:25]=[CH:26][C:15]([C:13](=[O:14])[CH2:12][NH:10][C@@H:7]([C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH2:8][OH:9])=[CH:16][C:17]=2[CH2:22][O:21]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-Phenylglycinol (28.9 g) was added in two portions to a solution of 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanone (40 g) and N,N-di-iso-propylethylamine (48.9 ml) in THF (500 ml) under nitrogen. After 4 h the resulting white precipitate was removed by filtration and the mother liquor concentrated in vacuo to give an orange oil. Acetonitrile (40 ml) was added and then removed in vacuo to give a light orange solid which was pulverised and triturated with cold acetonitrile (50 ml). The resulting solid was collected by filtration and washed with acetonitrile (2×30 ml) to give the title compound (38.5 g) as a white solid.
Workup
- customAfter 4 h the resulting white precipitate was removed by filtration
- concentrationthe mother liquor concentrated in vacuo
- customto give an orange oil
- customremoved in vacuo
- customto give a light orange solid which
- customtriturated with cold acetonitrile (50 ml)
- filtrationThe resulting solid was collected by filtration
- washwashed with acetonitrile (2×30 ml)
Sources & evidence
- ORD record
- ord-7634879c56e44cb2b510048a3aa7ca2c
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911560B2
Reaction notes
Loading…