HCID 23635904, compound → Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylate

HRID 338084Notes

Reaction equation

HRID 338084 reaction equation
[CH2:1]([N:4]([CH2:15]/[CH:16]=[N:17]/[OH:18])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:2]=[CH2:3].Cl[O-].[Na+]>ClCCl>[N:17]1[O:18][CH2:3][CH:2]2[CH2:1][N:4]([C:5]([O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:14])[CH2:15][C:16]=12

Participants

4

Reactant 2

HCID 23635904HCID 23635904, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 86697896Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylateYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl N-allyl-N-[(2E)-2-hydroxyiminoethyl]carbamate (24 g, 96.6 mmol) in dichloromethane (338 mL) is treated drop wise over 10 minutes with a 5% w/w aqueous solution of sodium hypochlorite (106.08 mmol, 143.06 mL). The resultant mixture is stirred at room temperature overnight. The reaction is quenched with a 40% aqueous solution of sodium bisulfite (7 g). The organic layer is separated, dried over magnesium sulfate, and concentrated under vacuum. The crude product is purified over silica gel eluting with 5% ethyl acetate in hexanes to give the title compound (18 g, 75%). ES/MS (m/e): 247 (M+H).

Workup

  1. customThe reaction is quenched with a 40% aqueous solution of sodium bisulfite (7 g)
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product is purified over silica gel eluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f16b5d0b216e44f19709cf3f27b4e876
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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