Tetrahydrofuran → HCID 87176143, compound

HRID 239748Notes

Reaction equation

HRID 239748 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-d05d482ee46f4a7fb3a0d1a77ae09356
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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