rel-(3R,3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)-3-(methoxymethyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole → rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-methoxyethanol

HRID 1478734Notes

Reaction equation

HRID 1478734 reaction equation
[CH:1]1([C@@H:4]2[O:15][CH2:14][C@:7]3([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=4[F:23])[NH:8][O:9][C@@H:10]([CH2:11][O:12][CH3:13])[C@@H:6]3[CH2:5]2)[CH2:3][CH2:2]1>C(O)(=O)C.[Zn]>[NH2:8][C@@:7]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH2:14][O:15][C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[CH2:5][C@H:6]1[C@@H:10]([OH:9])[CH2:11][O:12][CH3:13]

Participants

4

Reactant 1

HCID 90253561rel-(3R,3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)-3-(methoxymethyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

Product 1

HCID 90253562rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-methoxyethanol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (2.22 g, 34.0 mmol) was added to a solution of rel-(3R,3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)-3-(methoxymethyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C39) (850 mg, 2.61 mmol) in acetic acid (9 mL), and the resulting mixture was allowed to cool to room temperature and stir for 5 hours. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to afford the product as an oil. Yield: 845 mg, 2.58 mmol, 99%. LCMS m/z 328.2 [M+H+].

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-639f681af56b401aa01f1d7f7f7f87ca
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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