Sodium Sulfite → Benzyl 2-methyl-1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

HRID 10348Notes

Reaction equation

HRID 10348 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13](=[CH:16][CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:23].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]2([O:23][CH:16]2[CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 544962743-Ethylidenepyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 21041146Benzyl 2-methyl-1-oxa-5-azaspiro[2.4]heptane-5-carboxylateYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-ethylidenepyrrolidine-1-carboxylic acid benzyl ester (Example A8, 0.65 g, 2.8 mmol) and 3-chloroperoxybenzoic acid (0.86 g, 5 mmol) in dichloromethane (15 mL) is stirred at room temperature for 3 hours. The excess peracid is decomposed by the addition of 10% sodium sulfite. The organic layer is washed with 5% sodium bicarbonate solution, dried over Na2SO4 and evaporated. The residue is purified by column chromatography (1:1 hexanes/ethyl acetate) to afford the title compound (0.310 g). 1H NMR (200 MHz, CDCl3): δ 7.36–7.26 (m, 5H), 5.14 (s, 2H), 3.73–3.55 (m, 3H), 3.34 (d. 1H), 3.20–3.13 (m, 1H), 2.26–2.11 (m, 1H), 1.90–1.62 (m, 1H), 1.33 (d, 3H).

Workup

  1. washThe organic layer is washed with 5% sodium bicarbonate solution
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue is purified by column chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2c40f5f2214f4dffa7218b5f4c2a3986
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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