Triethylamine → (1R,2R,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-8-(2-mesyloxyethyl)-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088163Notes

Reaction equation

Cl.[F:2][C:3]([F:34])([F:33])[C:4]1[CH:5]=[C:6]([CH2:14][O:15][C@@H:16]2[CH2:22][CH2:21][C@@H:20]3[N:23]([CH2:24][CH2:25][OH:26])[C@@:17]2([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19]3)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl>[F:13][C:10]([F:11])([F:12])[C:8]1[CH:7]=[C:6]([CH2:14][O:15][C@@H:16]2[CH2:22][CH2:21][C@@H:20]3[N:23]([CH2:24][CH2:25][O:26][S:43]([CH3:42])(=[O:45])=[O:44])[C@@:17]2([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:18][CH2:19]3)[CH:5]=[C:4]([C:3]([F:33])([F:2])[F:34])[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(1R*,2R*,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-8-(2-hydroxyethyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 67; 173 mg, 0.37 mmol) was dissolved in dichloromethane (2 ml) and cooled to 0° C. Triethylamine (0.062 ml, 0.44 mmol) was added followed by methanesulphonyl chloride (0.029 ml, 0.37 mmol). The mixture was extracted between water and dichloromethane (×3) and the organics dried (MgSO4) and concentrated in vacuo to give the title compound as a clear oil (201 mg, 100%).

Workup

extractionThe mixture was extracted between water and dichloromethane (×3)
dry with materialthe organics dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ebe3443b070e4c83833e42cbc284ac4b
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727249B2

Reaction notes

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