HCID 68562169, compound → 2-(S)-(2-Cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20368Notes

Reaction equation

HRID 20368 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]([CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[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]([CH2:23][CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68562169HCID 68562169, compound

Product 1

HCID 685596732-(S)-(2-Cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Add 20% palladium hydroxide on carbon (Pearlman's catalyst) (92 mg) to a solution of 5-(S)-benzyloxymethyl-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester (211 mg, 0.51 mmol) in absolute ethanol (25 mL) and hydrogenate in a Parr shaker at 40° C. for 18 hours at 60 psi. Filter and concentrate to give the desired compound which is used without further purification.

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-eaad4f159d36464ea4a6575a5d404f59
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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