Diazomethane → HCID 10421232, compound

HRID 1087721Notes

Reaction equation

HRID 1087721 reaction equation
[OH:1][C:2]1[C:6]2[CH2:7][N:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:10][CH2:11][C:5]=2[O:4][N:3]=1.[N+](=[CH2:18])=[N-]>CCOCC>[CH3:18][O:1][C:2]1[C:6]2[CH2:7][N:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:10][CH2:11][C:5]=2[O:4][N:3]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 178501918HCID 178501918, compound2×

Product 1

HCID 10421232HCID 10421232, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 490 mg (1.97 mmol) of methyl 3-hydroxy-5,6,7,8-tetrahydro-4H-isoxazolo[4,5-c]azepin-5-carboxylate (Formula II; Z=methoxycarbonyl, R3 =R4 =hydrogen) (P. Krogsgaard-Larsen, Acta Chem. Scand. B 31 (1977) 584-588) in ether (20 ml) was added an excess of diazomethane. The mixture was stirred at room temperature for 1 hour and the excess of diazomethane was destroyed by addition of glacial acetic acid. The mixture was evaporated in vacuo and the residue submitted to flash-chromatography on silica gel (eluent: toluene-ethyl acetate containing 1% of glacial acetic acid) yielding 270 mg of the title compound as a colourless oil. The oil was crystallized from toluene-light petroleum giving the analytically pure title compound. M.P. 68°-70° C. 1H NMR (CDCl3): δ4.25 (2H, s), 3.93 (3H, s), 3.66 (5H, m), 2.83 (2H, t), 1.91 (2H, m).

Workup

  1. customthe excess of diazomethane was destroyed by addition of glacial acetic acid
  2. customThe mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-4897b14d742f49188b455457db0b9a14
Source dataset
uspto-grants-1990_10
Patent number
US04960769

Reaction notes

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