3-[(3aR,5S,7aS)-5-Methyltetrahydro-1H-pyrano[3,4-c][1,2]oxazol-7a(7H)-yl]benzonitrile → 3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]benzonitrile

HRID 68403Notes

Reaction equation

HRID 68403 reaction equation
[CH3:1][C@@H:2]1[O:10][CH2:9][C@:5]2([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[NH:6][O:7][CH2:8][C@@H:4]2[CH2:3]1.N[C@]1(C2C=C(C=CC=2Cl)C#N)[C@H](CO)C[C@H](C)OC1>>[NH2:6][C@:5]1([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[C@H:4]([CH2:8][OH:7])[CH2:3][C@H:2]([CH3:1])[O:10][CH2:9]1

Participants

3

Reactant 2

HCID 867212993-[(3aR,5S,7aS)-5-Methyltetrahydro-1H-pyrano[3,4-c][1,2]oxazol-7a(7H)-yl]benzonitrileHCID 867213003-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]-4-chlorobenzonitrile

Product 1

HCID 867212983-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]benzonitrile

Procedure

3-[(3aR,5S,7aS)-5-Methyltetrahydro-1H-pyrano[3,4-c][1,2]oxazol-7a(7H)-yl]benzonitrile (C21) was converted to the product using the method described for the synthesis of 3-[(3S,4R,6S)-3-amino-4-(hydroxymethyl)-6-methyltetrahydro-2H-pyran-3-yl]-4-chlorobenzonitrile (C18) in Example 6. The resulting product was used in the next step without further purification. Yield: 105 mg, 0.426 mmol, 60%. LCMS m/z 247.1 [M+H+].

Workup

  1. customThe resulting product was used in the next step without further purification

Sources & evidence

ORD record
ord-9bdc6922540b4cfbbeaf76020823ffdc
Source dataset
uspto-grants-2014_09
Patent number
US08822456B2

Reaction notes

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