Sodium Carbonate → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 1529555Notes

Reaction equation

HRID 1529555 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([N:19]1[CH2:24][CH:23]=[CH:22][CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:16][C:15]([O:14][C:12]([N:19]1[CH2:20][CH2:21][CH:22]2[CH:23]([O:6]2)[CH2:24]1)=[O:13])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperoxybenzoic acid (2.96 g, 12.0 mmol) in DCM (20 mL) was added to a solution of N-boc-1,2,3,6-tetrahydropyridine (2.0 g, 10.9 mmol) in DCM (10 mL) at 0° C. The mixture was stirred at room temperature overnight and then a 10% solution of Na2S2O3 was added and the mixture basified with a saturated solution of Na2CO3. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid 1,1-dimethylethyl ester (2.18 g, 100% yield) that was used in the next step without further purification. C10H17NO3 GCMS (EI): Rt 8.96, MW (theor) 199; m/z [M]+ 199 (using method, GC-MS Method 1).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-d6038721fdd3474ba976e8f9e9457ec5
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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