Hydrochloric Acid → (3S,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-isopropyldihydrofuran-2-one hydrochloride

HRID 1694886Notes

Reaction equation

HRID 1694886 reaction equation
[N:1]([C@H:4]([C@H:14]1[O:18][C:17](=[O:19])[C@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15]1)[CH2:5][O:6]CC1C=CC=CC=1)=[N+]=[N-].[ClH:23].O1CCOCC1.[H][H]>C(O)C.[C].[Pd]>[ClH:23].[NH2:1][C@H:4]([C@H:14]1[O:18][C:17](=[O:19])[C@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15]1)[CH2:5][OH:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 54578739(3S,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 66645582(3S,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-isopropyldihydrofuran-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 10.12 g of (3S,5S)-5-[(S)-1-azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one obtained in Example (1e) (33.5 mmol), 16.7 ml of a solution of 4 N hydrochloric acid in dioxane (66.8 mmol) and 3.57 g of 10% palladium-carbon (50% wet) in ethanol (170 ml) was stirred under a hydrogen atmosphere at room temperature for six hours. Hydrogen in the reaction vessel was replaced by nitrogen, and then the reaction mixture was diluted with 170 ml of ethanol. Palladium-carbon was separated by filtration and washed with ethanol. The solvent was evaporated from the filtrate under reduced pressure to obtain 8.50 g of crude (3S,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-isopropyldihydrofuran-2-one hydrochloride.

Workup

  1. customPalladium-carbon was separated by filtration
  2. washwashed with ethanol
  3. customThe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d1165543dca6487cbf19144c8c6862b1
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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