m-Chloroperbenzoic acid → tert-Butyl N-(2-oxiranylmethyl)carbamate

HRID 1182277Notes

Reaction equation

HRID 1182277 reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:17]>ClCCl>[O:17]1[CH2:3][CH:2]1[CH2:1][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamate

Product 1

HCID 11062891tert-Butyl N-(2-oxiranylmethyl)carbamateYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 28.9 g (184 mmol) of tert-butyl allylcarbamate in 400 mL of dichloromethane was added 103 g (460 mmol) of 77% 3-chloroperoxybenzoic acid at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was filtered and the filtrate was concentrated. The residue was taken up in diethyl ether and washed with 5% sodium hydrosulfite (3×), saturated sodium bicarbonate (3×), brine (3×), and dried over anhydrous magnesium sulfate. Removal of solvent gave 21 g (66%) of tert-butyl 2-oxiranylmethylcarbamate as a liquid. 1H-NMR (400 MHz, CDCl3): δ 4.73 (br s, 1H), 3.53 (br s, 1H), 3.21 (m, 1H), 3.08 (br s, 1H), 2.77 (t, J=4 Hz, 1H), 2.58 (m, 1H), 1.43 (s, 9H).

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated
  3. washwashed with 5% sodium hydrosulfite (3×), saturated sodium bicarbonate (3×), brine (3×)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-5e8579c7d8f84767b8429ea631dd6fe9
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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