(2S,3S,5R)-5-[(1S,2S)-1-Benzyloxy-3-(3-benzyloxy-5-fluoro-phenyl)-2-dibenzylaminopropyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester → (2S,3S,5R)-5-[(1S,2S)-2-Amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20469Notes

Reaction equation

HRID 20469 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([O:47]CC2C=CC=CC=2)[C@@H:15]([N:32](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([O:24]CC3C=CC=CC=3)[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:55][CH2:56][C:57]([F:60])([F:59])[F:58])[C@@H:9]1[CH3:61])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)(C)(C)C.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:47])[C@@H:15]([NH2:32])[CH2:16][C:17]2[CH:18]=[C:19]([OH:24])[CH:20]=[C:21]([F:23])[CH:22]=2)[CH2:12][O:11][C@@H:10]([O:55][CH2:56][C:57]([F:60])([F:58])[F:59])[C@@H:9]1[CH3:61])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 68560169(2S,3S,5R)-5-[(1S,2S)-1-Benzyloxy-3-(3-benzyloxy-5-fluoro-phenyl)-2-dibenzylaminopropyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 68560206(2S,3S,5R)-5-[(1S,2S)-2-Amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl esterYield 115.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

Add 20% palladium hydroxide on carbon (200 mg) to a solution of (2S,3S,5R)-5-[(1S,2S)-1-benzyloxy-3-(3-benzyloxy-5-fluoro-phenyl)-2-dibenzylamino-propyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester (116 mg, 0.138 mmol) in tert-butanol (10 mL). Heat to 45° C. and hydrogenate at 50 psi hydrogen gas for 18 hours. Filter and evaporate to give the desired compound (77 mg). MS(ESI): m/z=483 [M+H]+.

Workup

  1. filtrationFilter
  2. customevaporate

Sources & evidence

ORD record
ord-ad2afbf3c73b470db57c2c76204eb2ad
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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