Allylamine → (2R)-1-(Phenylmethoxy)-3-(2-propen-1-ylamino)-2-propanol

HRID 1486792Notes

Reaction equation

HRID 1486792 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.[CH2:13]([NH2:16])[CH:14]=[CH2:15]>>[CH2:13]([NH:16][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)[CH:14]=[CH2:15]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 159746(-)-Benzyl (R)-glycidyl ether

Product 1

HCID 118006903(2R)-1-(Phenylmethoxy)-3-(2-propen-1-ylamino)-2-propanolYield 100%

Conditions

Temperature
50 °C

Procedure

A 22 L reactor was charged with (2R)-benzyl 2-epoxypropyl ether (0.7692 kg, 4.684 mol) T-internal 18-19C. Allylamine (3800 mL, 51 mol) was added at 18-19° C. and resultant mixture was heated to 50° C. After 20 h, the mixture was concentrated, azeotroped with MTBE (4 L×3) to give (R)-1-(allylamino)-3-(benzyloxy)propan-2-ol, 7 (ca. 1037 g, 4.684 mol, 100% yield assumed) as colorless oil.

Workup

  1. concentrationthe mixture was concentrated
  2. customazeotroped with MTBE (4 L×3)

Sources & evidence

ORD record
ord-735949f8fdd4469ca26ae0cbc074d9d2
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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