Ammonia → 2-Propanol, 1-amino-3-(phenylmethoxy)-, (R)-

HRID 1486793Notes

Reaction equation

HRID 1486793 reaction equation
[O:1]1[CH2:12][C@@H:2]1[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH3:13]>CCO.CO.[OH-].[NH4+]>[NH2:13][CH2:12][C@@H:2]([OH:1])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 159746(-)-Benzyl (R)-glycidyl ether2×

Product 1

HCID 10786422-Propanol, 1-amino-3-(phenylmethoxy)-, (R)-

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of (2R)-benzyl 2-epoxypropyl ether, 6 (21.0 g, 0.128 mol) in EtOH (100 mL) was added slowly to a solution of 7.0 M ammonia in MeOH (100 mL) and 28% aq. ammonium hydroxide (210 mL) at rt. The reaction vessel was tightly capped and stirred at rt for 23 h. The completed reaction was concentrated in vacuo, and the crude product was azeotroped to dry twice with toluene (100 mL) to provide (R)-1-amino-3-(benzyloxy)propan-2-ol, 23 (23 g) as waxy solid containing approximately 15% of dimer. The crude was used for next reaction without further purification.

Workup

  1. customThe reaction vessel was tightly capped
  2. customThe completed reaction
  3. concentrationwas concentrated in vacuo
  4. customthe crude product was azeotroped
  5. dry with materialto dry twice with toluene (100 mL)

Sources & evidence

ORD record
ord-aa96cdd72b7946c8890e8ca04911def1
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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