Pyridine, hydrofluoride (1:1) → HCID 18646600, compound

HRID 2249122Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]2[O:19][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[FH:26].C(=O)(O)[O-].[Na+]>C(OCC)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:11]([F:26])[C@@H:10]1[OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (±)-(1S,2R,3R)-3-tert-butoxycarbonylamino-1,2-epoxy-1,2,3,4-tetrahydro-naphthalene (100 mg) in anhydrous diethyl ether (6 ml) cooled in an ice-bath was added 70% hydrogen fluoride-pyridine (0.24 ml). The mixture was stirred at 0° C. for 9 hours, ice was added and the reaction mixture was neutralized by addition of solid sodium bicarbonate (1.2 g) at 0° C. and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and evaporated to afford the crude title compound as an oil (65 mg). This crude material was purified by chromatography on silica gel (10 g, elution with ethyl acetate:cyclohexane, 2:8) and the resulting material (35 mg) was crystallized from a diethyl ether/pentane mixture to afford the title compound as a white solid, m.p. 98°-99° C.

Workup

additionice was added
extractionextracted with diethyl ether
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated
customto afford the crude title compound as an oil (65 mg)
customThis crude material was purified by chromatography on silica gel (10 g, elution with ethyl acetate:cyclohexane, 2:8)
customthe resulting material (35 mg) was crystallized from a diethyl ether/pentane mixture

Sources & evidence

ORD record: ord-de92fc61e631429496c15f6e8d695400
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05041673

Reaction notes

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