m-Chloroperbenzoic acid → Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 877675Notes

Reaction equation

HRID 877675 reaction equation
[N:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>ClCCl.C(=O)(O)[O-].[Na+]>[CH:3]12[O:24][CH:4]1[CH2:5][N:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2]2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To solution of benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate (10.0 g, 49.2 mmol) in dichloromethane (197 mL) at 0° C. was added m-CPBA (16.98 g, 98 mmol) in several portions and the resulting mixture was allowed to warm to rt and stir overnight. The resulting white heterogeneous mixture obtained was diluted with dichloromethane (150 mL) and aq. sat. sodium bicarbonate (150 mL). The mixture was stirred and the resulting layers were separated and the organic portion was washed successively with aq. sat. sodium bicarbonate (150 mL), water, brine, before drying over anhyd. sodium sulfate, filtering and concentrating in vacuo to a colorless oil (˜14 g). This crude material was subjected to purification by preparative chromatography using Hex/EtOAc mixtures as the eluant and an 80 g silica gel cartridge. Fractions containing the major product were combined and concentrated to afford the title compound (9.60 g, 43.8 mmol, 89%) as a colorless oil. LCMS: 220.2 (M+H)+; 1H NMR (400 MHz, METHANOL-d4): δ 7.41-7.31 (m, 4H), 5.14 (d, J=1.1 Hz, 2H), 3.84-3.74 (m, 4H), 3.42 (t, J=13.8 Hz, 2H).

Workup

  1. customThe resulting white heterogeneous mixture obtained
  2. stirringThe mixture was stirred
  3. customthe resulting layers were separated
  4. washthe organic portion was washed successively with aq. sat. sodium bicarbonate (150 mL), water, brine
  5. custombefore drying over anhyd
  6. filtrationsodium sulfate, filtering
  7. concentrationconcentrating in vacuo to a colorless oil (˜14 g)
  8. customThis crude material was subjected to purification by preparative chromatography
  9. additionFractions containing the major product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5a07c5a796814221a64641bb3e6a996b
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…