HCID 86706748, compound → (S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(hydroxymethy)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl)ethanone

HRID 710045Notes

Reaction equation

HRID 710045 reaction equation
[Si](OCC1ON=C([C@@H]2CCCN2C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)C=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[Si]([O:63][CH2:64][C:65]1[O:69][C:68]([C@@H:70]2[CH2:74][CH2:73][CH2:72][N:71]2[C:75](=[O:90])[C:76]([F:89])([F:88])[C:77]2([OH:87])[CH2:82][C:81]([CH3:84])([CH3:83])[CH2:80][C:79]([CH3:86])([CH3:85])[CH2:78]2)=[N:67][N:66]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[F:89][C:76]([F:88])([C:77]1([OH:87])[CH2:78][C:79]([CH3:86])([CH3:85])[CH2:80][C:81]([CH3:84])([CH3:83])[CH2:82]1)[C:75]([N:71]1[CH2:72][CH2:73][CH2:74][C@H:70]1[C:68]1[O:69][C:65]([CH2:64][OH:63])=[N:66][N:67]=1)=[O:90]

Participants

3

Reactant 2

HCID 86706748HCID 86706748, compoundHCID 86706758(S)-1-(2-(5-(((tert-Butyldiphenylsilyl)oxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl)-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone

Product 1

HCID 86706757(S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(hydroxymethy)-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl)ethanoneYield 86.7%

Procedure

The procedure of Example 3-(4) was repeated, except that the compound obtained in Example 3-(3) was replaced by the compound (1.378 g) obtained in Example 9-(4); this gave the titled compound (750 mg, colorless solid.)

Sources & evidence

ORD record
ord-73472313bac244b282f088d44ff18315
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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