8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → Tropine-3-mesylate

HRID 1464608Notes

Reaction equation

HRID 1464608 reaction equation
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:1][N:2]1[C@@H:6]2[CH2:7][CH:8]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:9][C@H:3]1[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 16125705Tropine-3-mesylateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tropine (14.2 g, 100 mmol) was dissolved in CH2Cl2 (210 ml) and triethylamine (23 ml, 160 mmol) was added. Methanesulfonyl chloride (9.3 ml, 120 mmol) was added rapidly dropwise which caused the methylene chloride solution to reflux gently. The mixture was stirred one hour further; then extracted with cold 0.5 molar sodium hydroxide, water, and brine, dried by filtration through phase separating paper and concentrated to yield 13.8 g (65%) of title product as a yellow solid. NMR 4.88 (t, J=5 Hz, 1H), 3.10-3.05 (m, 2H), 2.94 (s, 3H), 2.22 (s, 3H), 2.20-2.10 (m, 2H), 2.02-1.88 (m, 6H).

Workup

  1. temperatureto reflux gently
  2. extractionthen extracted with cold 0.5 molar sodium hydroxide, water, and brine
  3. customdried by filtration through phase
  4. customseparating paper
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8611fe045ee8454fb094e4e5800b87ca
Source dataset
uspto-grants-1994_04
Patent number
US05306723

Reaction notes

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