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

HRID 1478733Notes

Reaction equation

HRID 1478733 reaction equation
[CH:1]1([C@@H:4]2[O:15][CH2:14][C:7]3=[N:8][O:9][C@@H:10]([CH2:11][O:12][CH3:13])[C@@H:6]3[CH2:5]2)[CH2:3][CH2:2]1.C1([C@@H]2OC[C@]3([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=4[F:35])NOC[C@@H]3C2)CC1>>[CH:1]1([C@@H:4]2[O:15][CH2:14][C@:7]3([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=4[F:35])[NH:8][O:9][C@@H:10]([CH2:11][O:12][CH3:13])[C@@H:6]3[CH2:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 90253552rel-(3R,3aR,5R)-5-cyclopropyl-3-(methoxymethyl)-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazoleHCID 118621161HCID 118621161, compound

Product 1

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

Procedure

rel-(3R,3aR,5R)-5-Cyclopropyl-3-(methoxymethyl)-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole (C38) was converted to the product using the method described for synthesis of rel-(3aR,5R,7aS)-5-cyclopropyl-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C19) in Example 2. The product was obtained as an oil. Yield: 0.85 g, 2.6 mmol, 55%. LCMS m/z 326.2 [M+H+].

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-ff41c4fa51bb4c358aff9f04ce010b75
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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