Propane sultone → HCID 87176082, compound

HRID 239747Notes

Reaction equation

HRID 239747 reaction equation
[NH2:1][C@@H:2]([CH2:11][O:12][CH3:13])[C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH2:14]1[CH2:20][S:17](=[O:19])(=[O:18])[O:16][CH2:15]1>O1CCCC1.O>[OH:4][C@@H:3]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C@H:2]([NH:1][CH2:15][CH2:14][CH2:20][S:17]([OH:19])(=[O:18])=[O:16])[CH2:11][O:12][CH3:13]

Participants

5

Reactant 2

HCID 14264Propane sultoneHCID 5324726(1S,2S)-(+)-2-Amino-3-methoxy-1-phenyl-1-propanol

Product 1

HCID 87176082HCID 87176082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol (1.0 g, 5.5 mmol) in tetrahydrofuran (10 mL) was slowly added 1,3-propane sultone (662 mg, 5.3 mmol). The mixture was stirred at reflux for 2.5 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 80% Acetone/EtOH. 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 EG (1.0 g, 63%). 1H NMR (D2O, 500 MHz) δ ppm 7.32 (m, 5H), 4.77 (d, 1H, J=9.8 Hz), 3.53 (m, 1H), 3.37 (m, 1H). 3.26 (m, 1H), 3.17 (m, 6H), 2.91 (t, 2H, J=7.3 Hz), 2.07 (m, 2H). 13C NMR (D2O, 125 MHz) δ ppm 139.09, 129.33, 129.27, 127.11, 70.85, 66.29, 62.62, 58.76, 48.14, 44.24, 21.47. [α]D=+42.6° (c=0.00091 in water), ES-MS 302 (M−1).

Workup

  1. temperatureat reflux for 2.5 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 EG (1.0 g, 63%)

Sources & evidence

ORD record
ord-7b55213bca4b4fae88788404f8db81a1
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Reaction notes

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