8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → HCID 21186581, compound

HRID 1384323Notes

Reaction equation

HRID 1384323 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.[F:18][C:19]([F:25])([F:24])[S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[F:18][C:19]([F:25])([F:24])[S:20]([O:10][CH:8]1[CH2:9][CH:3]2[N:2]([CH3:1])[CH:6]([CH2:5][CH2:4]2)[CH2:7]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 21186581HCID 21186581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tropine (14.2 g, 0.10 mol) was dissolved in methylene chloride (210 mL) and triethylamine (23 mL, 0.16 mol). Trifluoromethanesulfonyl chloride (9.3 mL, 0.12 mol) was added dropwise at a rate such that the methylene chloride boiled gently. The reaction was stirred at ambient temperature for 1 h; then it was washed with cold 0.5 N sodium hydroxide, water, and brine. The organic phase was dried and concentrated to a yellow solid which had: NMR δ4.88 (t, 1 H), 3.10-3.05 (m, 2 H), 2.94 (s, 3 H), 2.22 (s, 3 H), 2.20-2.10 (m, 2 H), 2.02-1.88 (m, 6 H).

Workup

  1. washthen it was washed with cold 0.5 N sodium hydroxide, water, and brine
  2. customThe organic phase was dried
  3. concentrationconcentrated to a yellow solid which

Sources & evidence

ORD record
ord-0238d10af7474aa2a5b949797988097b
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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