Nitrogen → (2R,4R)-4-Cyclohexyl-1,2,3,4-tetrahydronaphthalen-2-yl 4-methylbenzenesulfonate

HRID 571171Notes

Reaction equation

HRID 571171 reaction equation
[CH:1]1([C@@H:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C@H:9]([OH:17])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.N#N>N1C=CC=CC=1>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:17][C@@H:9]2[CH2:8][C@H:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 73974-Toluenesulfonyl chlorideHCID 66645245(2R,4R)-4-cyclohexyl-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 86666517(2R,4R)-4-Cyclohexyl-1,2,3,4-tetrahydronaphthalen-2-yl 4-methylbenzenesulfonateYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Wyrick S D, Booth R G, Myers A M, Owens C E, Kula N S, Baldessarini R J, McPhail A T, and Mailman R B (1993) Synthesis and pharmacological evaluation of 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as ligands for a novel receptor with sigma-like neuromodulatory activity. J Med Chem 36:2542-2551) (2R,4R)-4-Cyclohexyl-1,2,3,4-tetrahydronaphthalen-2-ol 2a (0.23 g, 0.1 mol), p-toluenesulfonyl chloride (0.20 g, 0.11 mol), and pyridine (1.5 mL) was stirred in solution for 24 hours at rt, under inert atmosphere (N2). The solvent was removed and the crude material was purified by column chromatography (Si-gel) to give 3a in a 62% yield. HRMS m/z Calcd for C23H28O3S 407.1651 [M+Na]+. Found 407.1631.

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by column chromatography (Si-gel)

Sources & evidence

ORD record
ord-6017cafbfc1b4111a8994c990421065f
Source dataset
uspto-grants-2015_05
Patent number
US09024071B2

Reaction notes

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