m-Chloroperbenzoic acid → 1,1-Dimethylethyl 4-hydroxy-4-(2-oxiranylmethyl)-1-piperidinecarboxylate

HRID 1511782Notes

Reaction equation

HRID 1511782 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][CH:16]=[CH2:17])([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:26])C=1>C(Cl)Cl.P([O-])([O-])([O-])=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:14])([CH2:15][CH:16]2[CH2:17][O:26]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 186702981,1-Dimethylethyl 4-hydroxy-4-(2-oxiranylmethyl)-1-piperidinecarboxylateYield 26.7%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-allyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (3.1 g, 12.8 mmol, prepared according to J. Comb. Chem. 2002, 4, 125) in DCM and 0.3 M phosphate buffer (pH 8, 150 mL) was treated with mCPBA (3.5 g, 1.1 eq, 70%) and the mixture vigorously stirred at rt overnight. Further 3.5 g of mCPBA were added. After a total of 24 h, the phases were separated, the org. phase dried over MgSO4 and concentrated. CC (hex/EA 2:1 to 1:1 to EA) gave the desired intermediate as colourless oil (0.88 g, 26%).

Workup

  1. customAfter a total of 24 h, the phases were separated
  2. dry with materialphase dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9e4f394a639f4beeb359fb6fcf16de52
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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