Tetrabutylammonium Fluoride → (2S,5S)-2-Ethoxy-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20340Notes

Reaction equation

HRID 20340 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH2:12][O:11][C@H:10]([O:23][CH2:24][CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][OH:15])[CH2:12][O:11][C@H:10]([O:23][CH2:24][CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68562682HCID 68562682, compound

Product 1

HCID 68560702(2S,5S)-2-Ethoxy-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl esterYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (2S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester (0.39 g, 1.04 mmole) in tetrahydrofuran (3 mL) and add tetrabutylammonium fluoride (2.1 mL, 2.1 mmol, 1.0 M in tetrahydrofuran). Stir 45 minutes at room temperature, concentrate and purify (silica gel chromatography, eluting with 10:90 to 40:60 ethyl acetate:hexanes) to give the desired compound (252 mg, 92%).

Workup

  1. concentrationconcentrate
  2. custompurify
  3. wash(silica gel chromatography, eluting with 10:90 to 40:60 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-30ba77b1927543558b8fabc922a273c9
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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