Tetrahydrofuran → HCID 87176143, compound

HRID 2219757Notes

Reaction equation

HRID 2219757 reaction equation
[CH3:1][CH:2]1[CH:10]([NH2:11])[CH2:9][CH:5]2[C:6]([CH3:8])([CH3:7])[CH:3]1[CH2:4]2.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1.O1CCC[CH2:20]1>O>[CH3:20][C@:3]12[CH2:4][C@H:5]([C:6]1([CH3:7])[CH3:8])[CH2:9][C@@H:10]([NH:11][CH2:13][CH2:12][CH2:18][S:15]([OH:14])(=[O:17])=[O:16])[C@@H:2]2[CH3:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14264Propane sultoneHCID 4265892,6,6-Trimethyl-bicyclo[3.1.1]hept-3-ylamine

Product 1

HCID 87176143HCID 87176143, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (1R,2R,3R,5S)-(−)-isopinocampheylamine (2.0 g, 13.0 mmol) in tetrahydrofuran (20 mL) was slowly added 1,3-propanesultone (1.56 g, 12.5 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid product was collected by filtration, washed with acetone (2×25 mL), and dried in a vacuum oven (50° C.), to afford compound EH (2.7 g, 80%). 1H NMR (DMSO, 500 MHz) δ ppm 3.32 (m, 2H), 3.09 (d, 2H), 2.67 (m, 2H), 2.30 (m, 2H), 1.96 (m, 4H), 1.75 (m, 2H), 1.18 (s, 3H), 1.11 (m, 4H), 0.90 (s, 3H). 13C NMR (DMSO, 125 MHz) δ ppm 55.97, 50.11, 47.55, 45.86, 41.15, 40.91, 38.94, 32.81, 31.61, 27.96, 23.85, 22.59, 21.21, [α]D=−17.2° (c=0.00083 in water), ES-MS 274 (M−1).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid product was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. customdried in a vacuum oven (50° C.)
  5. customto afford compound EH (2.7 g, 80%)

Sources & evidence

ORD record
ord-6589c59aa8c340039a584c218ba79abe
Source dataset
uspto-grants-2008_08
Patent number
US07414076B2

Reaction notes

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