m-Chloroperbenzoic acid → Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine

HRID 1722268Notes

Reaction equation

HRID 1722268 reaction equation
[C:1]([NH:8][C@@H:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:10]=[CH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[C:1]([NH:8][C@H:9]([CH:10]1[CH2:11][O:27]1)[CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15601530Boc-1(S)-cyclohexylmethylprop-2-en-1-ylamine

Product 1

HCID 13892786Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.6 g of Boc-1(S)-cyclohexylmethylprop-2-en-1-ylamine are dissolved in 50 ml of CH2Cl2, and 1.9 g of m-chloroperbenzoic acid in 50 ml of CH2Cl2 are added dropwise at 0° C. The reaction solution is stirred at R.T. for 36 h and is then extracted first with 100 ml of 5% strength aqueous Na2SO3 solution and then with 100 ml of saturated aqueous Na2CO3 solution. Drying over Na2SO4 and concentration in vacuo are followed by chromatography on silica gel (mobile phase MTB/cyclohexane 1:1) resulting in the title compound as a colorless oil, diastereomer ratio 3:1 to 5:1.

Workup

  1. extractionis then extracted first with 100 ml of 5% strength aqueous Na2SO3 solution
  2. dry with materialDrying over Na2SO4 and concentration in vacuo

Sources & evidence

ORD record
ord-b04fcac3db7d40ffa9f97c52862ce39a
Source dataset
uspto-grants-1989_08
Patent number
US04855286

Reaction notes

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