Water → HCID 86614059, compound

HRID 1727178Notes

Reaction equation

[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([OH:10])[CH2:6]2.[CH2:11](N(CC)CC)C.C[S:19](Cl)(=[O:21])=[O:20].[OH2:23]>ClCCl>[S:19]([O:10][CH:5]1[CH2:4][CH:3]2[N:2]([CH3:1])[CH:7]([CH2:8][CH2:9]2)[CH2:6]1)([O:21][CH3:11])(=[O:20])=[O:23]

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 8-methyl-8-azabicyclo[3.2.1]octan-3-ol (299 g, 2.12 moles) in dichloromethane (3.5 l) was added triethylamine (445 ml, 3.2 moles) and the reaction mixture was cooled to −40° C. Methanesulfonyl chloride (293 g, 2.55 moles) was added dropwise over 90 min and the reaction mixture was then allowed to warm to room temperature. Water (1 l) was added and the organic extract washed with sodium-hydroxide (0.5M) water and saturated sodium chloride solution. The organic extracts were dried (Na2SO4) and concentrated in vacuo to give a yellow solid (262 g, 56%). The solid was recrystallised from hexane to give a first crop of the title compound as light yellow crystals (126.5 g, 27%), followed by a second crop (76.1 g, 16%).

Workup

temperatureto warm to room temperature
extractionthe organic extract
washwashed with sodium-hydroxide (0.5M) water and saturated sodium chloride solution
dry with materialThe organic extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b0c42024a3e1483290d15a6917f891cb
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07494992B2

Reaction notes

Loading…