[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol → HCID 90253458, compound

HRID 1478761Notes

Reaction equation

HRID 1478761 reaction equation
[CH:1]1([CH2:4][C@@H:5]2[O:13][CH2:12][C@:8]3([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=4[F:21])[NH:9][O:10][CH2:11][C@@H:7]3[CH2:6]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>>[NH2:9][C@@:8]1([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:12][O:13][C@@H:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH2:6][C@H:7]1[CH2:11][OH:10]

Participants

3

Reactant 2

HCID 71277793[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanolHCID 90253493HCID 90253493, compound

Product 1

HCID 90253458HCID 90253458, compoundYield 90.5%

Procedure

rel-(3aR,5S,7aS)-5-(Cyclopropylmethyl)-7a-(2,4-difluorophenyl) hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C70) (1.1 g, 4.09 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 (1.1 g), which was taken directly to the following step without additional purification.

Sources & evidence

ORD record
ord-4fd68ba356ff4c5fa8c0b7e5de6d87da
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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