Potassium Hydroxide → (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

HRID 1290017Notes

Reaction equation

HRID 1290017 reaction equation
[C:1]([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:13]([OH:16])[CH2:14]Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH-].[K+]>C(O)C>[C:1]([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:13]1[O:16][CH2:14]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10860587Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Product 1

HCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Cbz-3-(S)-amino-1-chloro-4-phenyl-2(S)-butanol (9.5 gm, 28 mmol) was added to a solution of KOH (1.9 gm, 34 mmol) in absolute ethanol (250 mL). After 15 minutes the solvent was removed and the residue dissolved in CH2C12 (100 mL). The organic solution was washed with water (100 mL) and dried (MgSO4). Filtration and concentration afforded a white solid, 7.4 gm (87%). Anal. Calc'd for C18H19NO3 : C, 72.71; H, 6.44; N, 4.71. Found: C, 72.16; H, 6.42; N, 4.65.

Workup

  1. customAfter 15 minutes the solvent was removed
  2. dissolutionthe residue dissolved in CH2C12 (100 mL)
  3. washThe organic solution was washed with water (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration
  6. customafforded a white solid, 7.4 gm (87%)

Sources & evidence

ORD record
ord-1696ae61e4c343efb8249be1bd6a8d8b
Source dataset
uspto-grants-1998_05
Patent number
US05750648

Reaction notes

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