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

HRID 1871935Notes

Reaction equation

HRID 1871935 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 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: Serinol (24 g) was added to a solution of trityl chloride (65 g) and triethylamine (51.0 g) in 600 mL of dry DMF. After stirring at room temperature for 48 h, the reaction was poured into water and extracted several times with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to dryness to afford N-triphenylmethylserinol (71.0 g).

Workup

  1. extractionextracted several times with diethyl ether
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-429cfd9f4b9c4f54aabeb348e8cecd62
Source dataset
uspto-grants-2000_08
Patent number
US06107300

Reaction notes

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