Triethylamine → Tert-butyl 3-(methanesulfonyloxy)-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1518551Notes

Reaction equation

[OH:1][CH:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:24][S:25]([O:1][CH:2]1[CH2:3][CH:4]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:7]([CH2:6][CH2:5]2)[CH2:8]1)(=[O:27])=[O:26]

Participants

Conditions

Temperature: 5 °C

Procedure

3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester (7.55 g, 33.2 mmol), triethylamine (5.1 mL, 37 mmol), and 4-dimethylaminopyridine (36 mg, 0.3 mmol) was dissolved in 100 mL of dichloromethane and cooled to 5° C. in an ice bath. Methanesulfonyl chloride (2.6 mL, 33.2 mmol) was added to the solution dropwise and the reaction warmed to room temperature and stirred at room temperature for 18 hours. The reaction was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent removed to afford 3-methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester as a clear yellow oil (10.2 g); 1H NMR (300 MHz, DMSO-d6): 5.09-5.01 (m, 1 H), 4.28 (s, 1 H), 4.22 (s, 1 H), 3.01 (s, 3 H), 2.20-1.97 (m, 6 H), 1.71-1.66 (m, 2 H), 1.46 (s, 9 H).

Workup

temperaturethe reaction warmed to room temperature
washThe reaction was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent removed

Sources & evidence

ORD record: ord-c19d207ea6f64757b5eafc084ce1f12b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232406B2

Reaction notes

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