(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OL → HCID 86682403, compound

HRID 2365253Notes

Reaction equation

HRID 2365253 reaction equation
[OH:1][C@H:2]1[CH2:7]CO[CH2:4][C@@H:3]1[N:8]1[CH2:16][C:15]2[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[C:12]([CH2:21][C:22]3[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)=[CH:11][C:10]=2[C:9]1=[O:30].N[C@@H]1[C@@H](O)CC[O:34][CH2:33]1>>[CH3:29][O:28][C:25]1[N:24]=[CH:23][C:22]([CH2:21][C:12]2[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]3[CH2:16][N:8]([C@@H:3]4[C@@H:2]([OH:1])[CH2:7][O:34][CH2:33][CH2:4]4)[C:9](=[O:30])[C:10]=3[CH:11]=2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 55285677(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OLHCID 68631246HCID 68631246, compound

Product 1

HCID 86682403HCID 86682403, compound

Procedure

1,5-Anhydro-2,3-dideoxy-3-{5-[(6-methoxypyridin-3-yl)methyl]-3-oxo-1,3-dihydro-2H-benzo[e]isoindol-2-yl}-L-threo-pentitol was prepared employing the procedures described for the construction of 2-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]-5-[(6-methoxypyridin-3-yl)methyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one in Example 11, substituting (3R,4S)-4-aminotetrahydro-2H-pyran-3-ol for (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol.

Sources & evidence

ORD record
ord-94dce400ebd44003baea3f9a993644dd
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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