Methanol → HCID 15675406, compound

HRID 1461276Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[O:13][C:12]([C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].CO>N1C=CC=CC=1>[S:23]([O:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[O:13][C:12]([C:14]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)=[O:15])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1)([CH3:22])(=[O:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

In 70 ml of pyridine was dissolved 3.47 g (11.88 mmol) of Compound t and with ice-cooling, 1.9 ml (23.77 mmol) of methanesulfonyl chloride was added dropwise. The mixture was stirred at 0° C. for 4.5 hours and, after addition of 5 ml of methanol, stirred at room temperature for 30 minutes. The solvent was then distilled off under reduced pressure and the residue was dissolved in 100 ml of methylene chloride. This solution was washed with 3 portions of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 4.04 g (91.8%) of 1-[5-(4-mesyloxypiperidinomethyl)-2-furancarbonyl]piperidine (Compound u) as red-brown oil.

Workup

temperaturewith ice-cooling
stirringstirred at room temperature for 30 minutes
distillationThe solvent was then distilled off under reduced pressure
dissolutionthe residue was dissolved in 100 ml of methylene chloride
washThis solution was washed with 3 portions of saturated aqueous sodium chloride solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-59f806c663cd4b3ea2b2cb3911e41023
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075301

Reaction notes

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