HCID 68561777, compound → (2R,3S,5S)-2-(2,2-Dimethylpropoxy)-5-hydroxymethyl-3-methylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20402Notes

Reaction equation

HRID 20402 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][O:15]CC2C=CC=CC=2)[CH2:12][O:11][C@@H:10]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C@@H:9]1[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[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][C:25]([CH3:28])([CH3:27])[CH3:26])[C@@H:9]1[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 68561777HCID 68561777, compound

Product 1

HCID 68563537(2R,3S,5S)-2-(2,2-Dimethylpropoxy)-5-hydroxymethyl-3-methylmorpholine-4-carboxylic acid tert-butyl esterYield 93.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Stir (2R,3S,5S)-5-benzyloxymethyl-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (0.65 g, 1.59 mmol) and 20% palladium hydroxide on carbon (0.65 g) in methanol (25 mL) under a hydrogen atmosphere at room temperature for 2 hours. Filter through Celite®, concentrate and purify (silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes) to give the desired compound as an oil (471 mg 93.0%).

Workup

  1. filtrationFilter through Celite®
  2. concentrationconcentrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-118dfd914ac040a6b292d60dad67639f
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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