2-Amino-2-methyl-1,3-propanediol → HCID 19806415, compound

HRID 1681340Notes

Reaction equation

HRID 1681340 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[NH2:16][C:17]([CH3:22])([CH2:20][OH:21])[CH2:18][OH:19]>CO.O>[CH3:22][C:17]([NH:16][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH:8]([OH:9])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH2:20][OH:21])[CH2:18][OH:19]

Participants

5

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 19806415HCID 19806415, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of trans-stilbene oxide (2.00 g, 0.010 mol) and 2-amino-2-methyl-1,3-propanediol (3.15 g, 0.030 mol) was heated at 150° C. for 3 hours. The reaction mixture was dissolved in 20 mL of methanol and diluted with water to form a white solid. The solid was collected, washed with water and dried for 18 hours under ambient conditions to obtain 2.46 g (82%) of the product. Recrystallization from toluene gave 2.38 g of material; mp 144°-145° C.

Workup

  1. customto form a white solid
  2. customThe solid was collected
  3. washwashed with water
  4. customdried for 18 hours under ambient conditions

Sources & evidence

ORD record
ord-4a91b569cb334470a9aacd79325b1d85
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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