Diethylamine → 1-[(3R,5R)-5-(3,4-difluorophenyl)morpholin-3-yl]ethanol

HRID 16386Notes

Reaction equation

HRID 16386 reaction equation
C1C2C(COC([N:18]3[C@@H:23]([CH:24]([OH:26])[CH3:25])[CH2:22][O:21][CH2:20][C@H:19]3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>C(#N)C.C1(C)C=CC=CC=1>[F:34][C:29]1[CH:28]=[C:27]([C@H:19]2[NH:18][C@@H:23]([CH:24]([OH:26])[CH3:25])[CH2:22][O:21][CH2:20]2)[CH:32]=[CH:31][C:30]=1[F:33]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 67373154HCID 67373154, compound

Product 1

HCID 673752911-[(3R,5R)-5-(3,4-difluorophenyl)morpholin-3-yl]ethanolYield 85.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R,5R)-3-(3,4-difluorophenyl)-5-(1-hydroxyethyl)morpholine-4-carboxylic acid 9H-fluorene-9-ylmethyl ester (950 mg) in acetonitrile (16 mL) was added diethylamine (4 mL), and the resultant solution was stirred for 1 hour at room temperature. The reaction solution was then diluted with toluene (20 mL), and solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 4/1→1/1), to thereby obtain the titled compound (424 mg). The physical properties of this crude product were as follows.

Workup

  1. customwas removed by distillation under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 4/1→1/1)

Sources & evidence

ORD record
ord-da9e9f379cbd4cbbbfe5eabe86cf0c58
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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