Ammonium Hydroxide → (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol

HRID 1665871Notes

Reaction equation

HRID 1665871 reaction equation
CC1C=CC(S([O:11][C@H:12]([C@@H:15]2[CH:19]=[CH:18][CH2:17][O:16]2)[CH2:13]O)(=O)=O)=CC=1.[OH-].[NH4+:21]>>[NH2:21][CH2:13][C@H:12]([C@@H:15]1[CH:19]=[CH:18][CH2:17][O:16]1)[OH:11]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 10401615(S)-1-((S)-2,5-Dihydrofuran-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Product 1

HCID 55281149(R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol

Conditions

Temperature
75 °C

Procedure

(S)-1-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate (14) (1.0 g, 3.52 mmol) was suspended in ammonium hydroxide (8 mL) then stirred and heated at 75° C. in a sealed tube for 6.5 hours during which time the two liquid phases became a single phase solution. The mixture was stood at ambient temperature for 2 days then the solvents were removed in vacuo. The residue was azeotroped with diethyl ether (3×10 mL) to obtain (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol which was used without further purification.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was azeotroped with diethyl ether (3×10 mL)

Sources & evidence

ORD record
ord-8900b7cf6de24cfbbc8a19b4d6360ed7
Source dataset
uspto-grants-2011_10
Patent number
US08039641B2

Reaction notes

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