3-Hydroxypiperidine → HCID 50923425, compound

HRID 1948503Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:27][CH:28]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:40]=[C:39]([C:41]3[C:45]([CH2:46][CH2:47][CH3:48])=[C:44]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[O:43][N:42]=3)[O:38][N:37]=2)=[CH:32][CH:31]=1)[OH:29]>CS(C)=O>[OH:29][CH:28]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:40]=[C:39]([C:41]3[C:45]([CH2:46][CH2:47][CH3:48])=[C:44]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[O:43][N:42]=3)[O:38][N:37]=2)=[CH:32][CH:31]=1)[CH2:27][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of piperidin-3-ol (20.04 mg, 0.198 mmol) in DMSO (2 mL) was added tetrabutylammonium hydroxide (0.198 mL, 0.198 mmol). After 5 minutes, 2-bromo-1-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol, Int-I-C (30 mg, 0.066 mmol) was added. The reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was filtered and purified by HPLC. HPLC conditions: PHENOMENEX® Luna C18 5 micron column (250×30 mm); 25-100% CH3CN/water (0.1% TFA); 25 minute gradient; 20 mL/min to yield 22 mg of 1-(2-hydroxy-2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-ol as the TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.16 (2H, d, J=8.13 Hz), 7.83 (2H, dd, J=8.02, 1.65 Hz), 7.58-7.73 (5H, m), 5.17-5.28 (1H, m), 4.10 (1H, d, J=14.72 Hz), 3.06-3.91 (5H, m), 2.95-3.06 (2H, m), 2.59-2.95 (2H, m), 1.77-2.21 (2H, m), 1.64-1.76 (2H, m), 1.16-1.42 (1H, m), 0.98 (3H, t, J=7.36 Hz). MS (m+1)=475. HPLC Peak RT=3.32 minutes (Analytical Method A). Purity=98%.

Workup

filtrationThe reaction mixture was filtered
custompurified by HPLC
custom25 minute

Sources & evidence

ORD record: ord-863b99a4ca6440478491b3ac71b27dd5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399451B2

Reaction notes

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