Propane sultone → HCID 11458776, compound

HRID 239751Notes

Reaction equation

HRID 239751 reaction equation
[NH2:1][C@@H:2]([CH:5]([CH3:7])[CH3:6])[CH2:3][OH:4].[CH2:8]1[CH2:14][S:11](=[O:13])(=[O:12])[O:10][CH2:9]1>O1CCCC1.O>[OH:4][CH2:3][C@@H:2]([NH:1][CH2:9][CH2:8][CH2:14][S:11]([OH:13])(=[O:12])=[O:10])[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 640993L-Valinol

Product 1

HCID 11458776HCID 11458776, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(−)-2-amino-3-methyl-1-butanol (2.50 g, 24.2 mmol) in tetrahydrofuran (35 mL) was slowly added 1,3-propane sultone (2.89 g, 23.0 mmol). The mixture was stirred at reflux for 3 h. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×25 mL). The crude product was suspended in 80% acetone/ethanol (75 mL). The suspension was stirred at reflux for 30 seconds. The solid product was collected by filtration, and dried in a vacuum oven (50° C.), to afford compound EP (2.9 g, 56%). 1H NMR (D2O, 500 MHz) δ ppm 3.78 (dd, 1H), 3.62 (dd, 1H), 3.13 (m, 2H), 2.90 (m, 1H), 2.88 (t, 3H), 1.90 (m, 3H), 0.90 (d, 3H), 0.84 (d, 3H). 13C NMR (D2O, 125 MHz) δ ppm 64.74, 57.24, 48.20, 44.44, 26.98, 21.49, 18.53, 17.00. [α]D=+4.1° (c=0.0017 in water), ES-MS 224 (M−1).

Workup

  1. temperatureat reflux for 3 h
  2. filtrationThe solid material was collected by filtration
  3. washwashed with acetone (2×25 mL)
  4. stirringThe suspension was stirred
  5. temperatureat reflux for 30 seconds
  6. filtrationThe solid product was collected by filtration
  7. customdried in a vacuum oven (50° C.)
  8. customto afford compound EP (2.9 g, 56%)

Sources & evidence

ORD record
ord-bc6f235134a74db38a08dc2235cdf758
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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