3-(Chloromethyl)pyridine → HCID 9846527, compound

HRID 345306Notes

Reaction equation

[H-].[Na+].[C:3]1([CH2:9][C@H:10]2[C@@:15]3([CH2:21][C:20](=[O:22])[NH:19][CH2:18][CH2:17][S:16]3(=[O:24])=[O:23])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Cl)[CH:26]=1>CS(C)=O.C(OCC)(=O)C>[C:3]1([CH2:9][C@H:10]2[C@@:15]3([CH2:21][C:20](=[O:22])[N:19]([CH2:31][C:27]4[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=4)[CH2:18][CH2:17][S:16]3(=[O:23])=[O:24])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred suspension of sodium hydride (5.5 g, 60% dispersion in mineral oil) in dimethyl sulfoxide (400 ml) was heated at 60° C. for 1 hour under nitrogen atmosphere. (1S,6S)-1-Phenylmethyl-11-oxo-7-thia-10-azaspiro[5.6]-dodecane 7,7-dioxide (40.0 g) and 3-pyridylmethyl chloride (25 g) were added to the nearly clear solution and the mixture was allowed to stand at room temperature for 15 minutes. The mixture was diluted with ethyl acetate (2 l) and washed with saturated aqueous sodium bicarbonate (2 l) and brine (2 l). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was triturated with ethyl acetate and recrystallized from ethanol to give (1S,6S)-1-phenylmethyl-10-(3-pyridylmethyl)-11-oxo-7-thia-10-azaspiro[5.6]dodecane 7,7-dioxide (14.0 g).

Workup

washwashed with saturated aqueous sodium bicarbonate (2 l) and brine (2 l)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was triturated with ethyl acetate
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-b33704b7f9fa4b49b5c8d563d4411ab4
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05057513

Reaction notes

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