Hexane → Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 1784794Notes

Reaction equation

HRID 1784794 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:22].CCCCCC.C(OCC)(=O)C>ClCCl>[CH:5]12[O:22][CH:4]1[CH2:3][CH2:2][N:1]([C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[CH2:6]2

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 13186888Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of benzyl 3,6-dihydropyridine-1(2H)-carboxylate (20.0 g, 92.0 mmol) in dichloromethane (280 ml) was cooled to 0° C. A solution of m-chloroperoxybenzoic acid (22.5 g, approx. 130 mmol) in dichloromethane (560 ml) was added drop-wise and the resulting colourless reaction mixture warmed to room temperature. After an additional 4 h at room temperature (reaction complete by tlc using 50:50 hexane:ethyl acetate as eluent.) the reaction mixture was washed with aqueous potassium carbonate solution (5 wt %, 3×200 ml) and brine (200 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to furnish benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate as a yellow oil (22.0 g; 100%).

Workup

  1. washwas washed with aqueous potassium carbonate solution (5 wt %, 3×200 ml) and brine (200 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b69f37ad842d46b3aeb6be2812aebbb8
Source dataset
uspto-grants-2009_03
Patent number
US07504419B2

Reaction notes

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