Methanol → HCID 178518978, compound

HRID 1277633Notes

Reaction equation

HRID 1277633 reaction equation
[Br-].[OH:2][C:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[O:5][NH+:4]=1.C(N(CC)CC)C.[K+].[Br-].CO>O.C(O)C>[O:5]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:11]=2[C:3]([OH:2])=[N:4]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 253877Potassium BromideHCID 700825683-Hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridinium bromide

Product 1

HCID 178518978HCID 178518978, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridinium bromide (77 mg; 0.35 mmol) in water (0.6 ml) was added a solution of triethylamine (39 mg; 0.39 mmol) in ethanol (0.6 ml). The mixture was left at 25° C. for 2 hours. Ia (42 mg; 86%) was isolated as colourless crystals, m.p. 242°-244° C. (decomp.). IR (KBr): 3700-2900 (s), 2900-1900 (several bands, m-s), 1670 (s), 1625 (m) cm-1. UV [methanol (log ε)]: 212 (3.64) nm. pKA values (H2O, 25° C.): 4.44±0.03, 8.48±0.04.

Workup

  1. customIa (42 mg; 86%) was isolated as colourless crystals, m.p. 242°-244° C. (decomp.)

Sources & evidence

ORD record
ord-6dc8ba7f16784d5aba90e25ad771b03c
Source dataset
uspto-grants-1981_07
Patent number
US04278676

Reaction notes

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