[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol → rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-fluoroethanol

HRID 1478740Notes

Reaction equation

HRID 1478740 reaction equation
[CH:1]1([C@@H:4]2[O:14][CH2:13][C@:7]3([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=4[F:22])[NH:8][O:9][C@@H:10]([CH2:11][F:12])[C@@H:6]3[CH2:5]2)[CH2:3][CH2:2]1.N[C@@]1(C2C=CC(F)=CC=2F)CO[C@@H](COCC2C=CC=CC=2)C[C@H]1CO>>[NH2:8][C@@:7]1([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:13][O:14][C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[CH2:5][C@H:6]1[C@@H:10]([OH:9])[CH2:11][F:12]

Participants

3

Reactant 2

HCID 71277793[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanolHCID 90253440rel-(3R,3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)-3-(fluoromethyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole

Product 1

HCID 90253568rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-fluoroethanol

Procedure

rel-(3R,3aR,5R,7aS)-5-Cyclopropyl-7a-(2,4-difluorophenyl)-3-(fluoromethyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C44) was converted to the product using the chemistry described for synthesis of [(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C6) in Preparation P1. The product was obtained as an oil. Yield: 0.17 g, 0.54 mmol, 99%. LCMS m/z 316.2 [M+H+].

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-1c989661525745a4be3e3c2212e7b6b3
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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