Phenylethanolamine → HCID 86754760, compound

HRID 1602047Notes

Reaction equation

HRID 1602047 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)O)=[O:6])[CH:2]=[CH2:3].NC[CH:19](C1C=CC=CC=1)[OH:20].CCN([CH2:32][CH3:33])CC.[CH2:34]([O:37][C:38](Cl)=[O:39])C=C>C(Cl)Cl>[CH3:34][O:37][C:38]([C:32]1[CH2:33][C:16]2[C:11]([CH2:9][C:8]=1[NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[CH:12][CH:13]=[CH:14][C:15]=2[O:20][CH3:19])=[O:39]

Participants

6

Reactant 4

HCID 1000PhenylethanolamineHCID 8471TriethylamineHCID 18052Allyl chloroformateHCID 15247504HCID 15247504, compound2×

Product 1

HCID 86754760HCID 86754760, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Synthesis of N-Allyloxycarbonyl-2-amino-1-phenylethanol (23) as illustrated in FIG. 5, reaction 4: ##STR12## Compound 23: Chemical method: 2-Amino-1-phenylethanol 15(0.50 g, 3.64 mmol) suspended in dry CH2Cl2 (20 mL) was treated with Et3N (triethylamine) (0.53 mL, 3.80 mmol) and allylchloroformate (0.41 mL, 3.86 mmol) for 30 min. The mixture was diluted with CH2Cl2 and washed with 1N KHSO4 and brine, dried (MgSO4), filtered and concentrated in vacuo. Silica gel column chromatography (eluent: CH2Cl2 /MeOH, 95/5, v/v) gave the desired product (742 mg) as a glass in 92% yield.

Workup

  1. customas illustrated in FIG. 5, reaction 4
  2. washwashed with 1N KHSO4 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e8279fcb9c84bd3aa4c2de1bf027e08
Source dataset
uspto-grants-1999_11
Patent number
US05981267

Reaction notes

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