m-Chloroperbenzoic acid → tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

HRID 263756Notes

Reaction equation

HRID 263756 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([NH:19][C@H:20]([CH:28]=[CH2:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(Cl)Cl>[C:12]([NH:19][C@H:20]([C@@H:28]1[CH2:29][O:9]1)[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11064740(S)-tert-Butyl 1-phenylbut-3-en-2-ylcarbamate

Product 1

HCID 9813904tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.74 g of m-chloroperbenzoic acid in 50 ml of methylene chloride is added over the course of 15 min at from 0° to 5° C. to a solution of 1.45 g of N-Boc-1-phenyl-3-buten-2(S)-amine in 20 ml of methylene chloride. The batch is stirred for 18 h at that same temperature and is then stirred for a further 8 h, with heating to RT, to complete the reaction and poured onto ice-cold 10% sodium carbonate solution. The aqueous phase is extracted three times with ether. The combined organic phases are washed in succession three times with 10% sodium sulfite solution, three times with saturated sodium hydrogen carbonate solution, with sodium thiosulfate solution and with brine and dried over sodium sulfate. After concentrating the solvents, the title compound is purified by column chromatography (SiO2, hexane/ethyl acetate: 4/1) and recrystallised from hexane. M.p. 51°-52° C.; TLC Rf (C)=0.33; FAB-MS (M+H)+=264.

Workup

  1. stirringis then stirred for a further 8 h
  2. customthe reaction
  3. additionpoured onto ice-cold 10% sodium carbonate solution
  4. extractionThe aqueous phase is extracted three times with ether
  5. washThe combined organic phases are washed in succession three times with 10% sodium sulfite solution, three times with saturated sodium hydrogen carbonate solution, with sodium thiosulfate solution and with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentrating the solvents
  8. customthe title compound is purified by column chromatography (SiO2, hexane/ethyl acetate: 4/1)
  9. customrecrystallised from hexane

Sources & evidence

ORD record
ord-83cec1ecf4cd4c9ea71659d9998b833b
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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