1-Phenylethanol → HCID 67179912, compound

HRID 885167Notes

Reaction equation

HRID 885167 reaction equation
[N@:1]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][CH:2]1[C:4]([O:6][CH3:7])=[O:5].[C:18]1([CH:24]([OH:26])[CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.B(F)(F)F.CCOCC>ClCCl>[CH3:7][O:6][C:4](=[O:5])[CH:2]([NH:1][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH2:3][O:26][CH:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:25]

Participants

5

Reactant 3

HCID 74091-PhenylethanolHCID 8000Boron trifluoride etherateHCID 4255958154632-86-7

Product 1

HCID 67179912HCID 67179912, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-benzyl 2-methyl(S)-(−)-1,2-aziridinedicarboxylate (1.88 g) in dichloromethane (30 ml) were added at 0° C. 1-phenyl-ethanol (9.77 g) and boron trifluoride etherate (2.0 ml). After stirring the mixture for one hour the cooling bath was removed and stirring was continued overnight. Then the reaction mixture was poured onto saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated. The crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0→90:10) to give S)-2-benzyloxycarbonylamino-3-(1-phenyl-ethoxy)-propionic acid methyl ester (1.34 g, 47%) as a light yellow oil. MS (ISP): 358.2 ([M+H]+)).

Workup

  1. customwas removed
  2. stirringstirring
  3. waitwas continued overnight
  4. additionThen the reaction mixture was poured onto saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0→90:10)

Sources & evidence

ORD record
ord-ea1b47a5bec94ca3ad77db0ffb3b428b
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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