1-Benzylamino-2-benzyloxyethane → HCID 59370738, compound

HRID 1873977Notes

Reaction equation

HRID 1873977 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:23]=[C:24]([C@@H:28]2[CH2:30][O:29]2)[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20]>CC(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:30][C@@H:28]([C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=1)[OH:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5624481-Benzylamino-2-benzyloxyethaneHCID 10986600HCID 10986600, compound

Product 1

HCID 59370738HCID 59370738, compoundYield 133.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-Benzyl-2-(benzyloxy)ethane amine (13.6532 g) which can be prepared according to the method described in Reference example 56, etc. was added with (R)-2-(3-nitrophenyl)oxirane (20.21 g) and 2-propanol (205 mL), followed by stirring for 36 hours at reflux. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Toluene (100 mL) was added to the residue and the mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography (“COLUMN-D”; n-hexane:ethyl acetate=85:15→80:20) to obtain the title compound (30.761 g).

Workup

  1. temperatureat reflux
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionToluene (100 mL) was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (“COLUMN-D”; n-hexane:ethyl acetate=85:15→80:20)

Sources & evidence

ORD record
ord-f68aea91e5b348fbbfd9720164f2a1c1
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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