Sodium Hydroxide → benzyl N-[(oxiran-2-yl)methyl]carbamate

HRID 1511786Notes

Reaction equation

HRID 1511786 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH:12]1[CH2:13][O:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 562279Benzyl allylcarbamate

Product 1

HCID 18471703benzyl N-[(oxiran-2-yl)methyl]carbamateYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of allyl-carbamic acid benzyl ester (9.6 g, 50 mmol) in DCM (250 mL) was treated with mCPBA (11.55 g, 50 mmol, 75% purity) and the mixture was stirred at rt for 4 h. The pH of the mixture was adjusted to 9 by addition of 1M aq. NaOH. The phases were separated and the org. phase dried over MgSO4 and concentrated. The residue was purified by CC (hex/EA 2:1) to give the desired intermediate (7.4 g, 71% yield) as a colourless oil.

Workup

  1. customThe phases were separated
  2. dry with materialphase dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by CC (hex/EA 2:1)

Sources & evidence

ORD record
ord-6cd8e41ef1e64d769294fc11d53d7a6d
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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