18-Crown-6 → HCID 68081530, compound

HRID 1748187Notes

Reaction equation

HRID 1748187 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH:12]2[CH2:13][CH:14]([OH:16])[CH2:15][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])[CH3:3].C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].Br[CH2:42][C:43]1[C:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[CH3:57])=[N:45][O:46][C:47]=1[CH:48]1[CH2:50][CH2:49]1>O1CCCC1.O.C(OCC)(=O)C>[CH:48]1([C:47]2[O:46][N:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=3[CH3:57])[C:43]=2[CH2:42][O:16][CH:14]2[CH2:15][CH:9]3[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:12]([CH2:11][CH2:10]3)[CH2:13]2)[CH2:50][CH2:49]1

Participants

8

Reactant 4

HCID 2855718-Crown-6HCID 21187725tert-Butyl 3-hydroxy-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 23665647Potassium tert-butoxideHCID 67983924HCID 67983924, compound

Product 1

HCID 68081530HCID 68081530, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A flask was purged with nitrogen and then charged with N-Boc-nortropine (1.64 g, 7.20 mmol), 18-crown-6 (1.59 g, 6.00 mmol), and anhydrous tetrahydrofuran (60 mL). Potassium tert-butoxide (1.34 g, 12.0 mmol) was added portion-wise, and the mixture was stirred vigorously under nitrogen for 1 hour. 4-(Bromomethyl)-5-cyclopropyl-3-(o-tolyl)isoxazole (1.75 g, 6.00 mmol) in tetrahydrofuran (20 mL, anhydrous) was added dropwise, and the reaction mixture was stirred for 1 hour under nitrogen. The solvent was reduced in vacuo and the mixture diluted with water (100 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The crude residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate/hexanes to yield the desired product as a yellow oil. MS m/z 439.2 (M+1).

Workup

  1. customA flask was purged with nitrogen
  2. stirringthe reaction mixture was stirred for 1 hour under nitrogen
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c8751aa526e1405594d83b3644ff4302
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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