Water → N-trityl-1,3-dihydroxy-2-propanamine

HRID 1871930Notes

Reaction equation

HRID 1871930 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.O>CN(C=O)C>[C:8]1([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 68294Serinol

Product 1

HCID 18427762N-trityl-1,3-dihydroxy-2-propanamineYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: Serinol (3.42 g) was added to a solution of trityl chloride (8.36 g) and triethylamine in 75 mL of dry DMF. After stirring at room temperature overnight, the reaction was poured into water and extracted twice with toluene. The combined organic layers were dried over potassium carbonate and concentrated to dryness. Recrystallization from boiling 1:1 benzene/hexane (two crops) afforded N-triphenylmethylserinol (7.59 g).

Workup

  1. extractionextracted twice with toluene
  2. dry with materialThe combined organic layers were dried over potassium carbonate
  3. concentrationconcentrated to dryness
  4. customRecrystallization

Sources & evidence

ORD record
ord-559136c8a4ee480bae041a04ca31a11b
Source dataset
uspto-grants-2000_08
Patent number
US06107300

Reaction notes

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