Allyl bromide → Tert-butyl (oxiran-2-ylmethoxy)carbamate

HRID 988339Notes

Reaction equation

HRID 988339 reaction equation
[CH2:1]([O:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH:2]=[CH2:3].[OH:13]NC(=O)OC(C)(C)C.[H-].[Na+].C(Br)C=C.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[O:13]1[CH2:3][CH:2]1[CH2:1][O:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 70297m-Chloroperbenzoic acidHCID 97534tert-butyl N-hydroxycarbamateHCID 22322878Carbamic acid, (2-propenyloxy)-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 18008120Tert-butyl (oxiran-2-ylmethoxy)carbamateYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to (16-1) described in Reference Example 16, 659 mg (3.80 mmol) of tert-butyl N-(allyloxy)carbamate prepared from tert-butyl N-hydroxycarbamate, sodium hydride and allyl bromide was dissolved in 10 ml of dichloromethane, and the thus prepared solution was mixed with 886 mg (4.67 mmol) of m-chloroperbenzoic acid and stirred at room temperature for 24 hours. The reaction solution was filtered, mixed with a 1 N sodium hydroxide aqueous solution and extracted with chloroform. The chloroform layer was washed with saturated brine and dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to obtain 447 mg (yield, 62%) of tert-butyl N-(2,3-epoxypropoxy)carbamate.

Workup

  1. filtrationThe reaction solution was filtered
  2. additionmixed with a 1 N sodium hydroxide aqueous solution
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8bfc4e3ba44d4596a52583c17d3ed270
Source dataset
uspto-grants-2003_10
Patent number
US06635662B2

Reaction notes

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