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

HRID 1478723Notes

Reaction equation

HRID 1478723 reaction equation
[CH:1]1([C@@H:4]2[O:13][CH2:12][C@:7]3([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=4[F:21])[NH:8][O:9][C@@H:10]([CH3:11])[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:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:12][O:13][C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[CH2:5][C@H:6]1[C@@H:10]([OH:9])[CH3:11]

Participants

3

Reactant 2

HCID 71277793[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanolHCID 90253542(3S,3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)-3-methylhexahydro-1H-pyrano[3,4-c][1,2]oxazole

Product 1

HCID 118621176(1S)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]ethanol

Procedure

(3S,3aR,5R,7aS)-5-Cyclopropyl-7a-(2,4-difluorophenyl)-3-methyl hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C28) was converted to the product using the method 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 resulting oil was used in the next step without additional purification. Yield: 0.11 g, 0.37 mmol, 87%. LCMS m/z 298.2 [M+H+].

Workup

  1. customThe resulting oil was used in the next step without additional purification

Sources & evidence

ORD record
ord-6012e8e1e00649839026042057f2846f
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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