HCID 68562982, compound → (2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20406

Reaction equation

HRID 20406 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])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>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])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 68562982HCID 68562982, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68564170(2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Stir (2R,5S)-5-benzyloxymethyl-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (7.05 g, 17.92 mmol) and 20% palladium hydroxide on carbon in methanol (150 mL) under 1 atmosphere of hydrogen gas at room temperature for 12 hours. Filter and concentrate to give the desired compound as a thick oil which is used directly in the next step without further purification (5.10 g).

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-b4a8cf8faafe4769ad32a73e4db765cb
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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