Acetonitrile → 1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanone

HRID 1593207Notes

Reaction equation

HRID 1593207 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]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 1347972-Amino-2-phenylethan-1-olHCID 11150315Ethanone, 2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-

Product 1

HCID 114733041-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (40g) and N,N-di-iso-propylethylamine (48.9 ml) in THF (500 ml) under nitrogen. After 4h 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

  1. customAfter 4h the resulting white precipitate was removed by filtration
  2. concentrationthe mother liquor concentrated in vacuo
  3. customto give an orange oil
  4. customremoved in vacuo
  5. customto give a light orange solid which
  6. customtriturated with cold acetonitrile (50 ml)
  7. filtrationThe resulting solid was collected by filtration
  8. washwashed with acetonitrile (2×30 ml)

Sources & evidence

ORD record
ord-e6ad2988dc2c4420ae29a36f95169a6c
Source dataset
uspto-grants-2007_11
Patent number
US07294725B1

Reaction notes

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