[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol → HCID 90253579, compound

HRID 1478750Notes

Reaction equation

HRID 1478750 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][C@@H:15]([C:18]3([CH3:21])[CH2:20][CH2:19]3)[CH2:14][C@H:13]1[CH2:12][O:11][NH:10]2.N[C@@]1(C2C=CC(F)=CC=2F)CO[C@@H](COCC2C=CC=CC=2)C[C@H]1CO>>[NH2:10][C@@:9]1([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:17][O:16][C@@H:15]([C:18]2([CH3:21])[CH2:20][CH2:19]2)[CH2:14][C@H:13]1[CH2:12][OH:11]

Participants

3

Reactant 2

HCID 71277793[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanolHCID 90253576HCID 90253576, compound

Product 1

HCID 90253579HCID 90253579, compoundYield 148%

Procedure

rel-(3aR,5R,7aS)-7a-(2,4-Difluorophenyl)-5-(1-methylcyclopropyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C57) (1.48 g, 5.00 mmol) was converted to the product according to the method described for the 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 a dark oil (2.2 g), which was taken directly to the following step without additional purification.

Sources & evidence

ORD record
ord-5b094f11307c4c4ab5c6d634cccc87c4
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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