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

HRID 446712Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

Compound 1010 (7.55 g, 33.2 mmol), triethylamine (5.1 mL, 37 mmol), and 4-dimethylaminopyridine (36 mg, 0.3 mmol) were taken into 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 under reduced pressure to afford 10.2 g of 3-methanesulfonyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester as a mixture of isomers (Compound 1011) as a clear yellow oil; 1H NMR (300 MHz, DMSO-d6): δ 5.09-5.01 (m, 1H), 4.28 (s, 1H), 4.22 (s, 1H), 3.01 (s, 3H), 2.20-1.97 (m, 6H), 1.71-1.66 (m, 2H), 1.46 (s, 9H). This compound was used without further purification.

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 under reduced pressure

Sources & evidence

ORD record: ord-d43b6ef7d43d450ba0ec5e6be47fbe4e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481524B2

Reaction notes

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