m-Chloroperbenzoic acid → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 869065Notes

Reaction equation

HRID 869065 reaction equation
Cl[C:2]1C=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.C=C1CC[N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])CC1>C(Cl)Cl>[C:22]([O:21][C:19]([N:16]1[CH2:2][CH2:3][C:4]2([O:10][CH2:8]2)[CH2:5][CH2:6]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27568081-Boc-4-Methylenepiperidine

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (1.14 g, 6.6 mmol) was added to a solution of tert-butyl 4-methylenepiperidine-1-carboxylate (1 g, 5.1 mmol) in CH2Cl2 (30 mL) at 0° C. The reaction mixture was stirred for 15 h at rt, diluted with CH2Cl2, washed with a saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4), and evaporated to afford 1.1 g of the title compound which was used without further purification. 1H-NMR (400 MHz, CDCl3) δ ppm 3.74-3.65 (m, 2H), 3.45-3.38 (m, 2H), 2.68 (s, 2H), 1.82-1.75 (m, 2H), 1.48-1.41 (m, 2H), 1.46 (s, 9H).

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-6d49a33d5fae42c184f25bec44374913
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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