Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 66605107, compound

HRID 2410776Notes

Reaction equation

HRID 2410776 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:12]=[C:11]([C:21]([NH2:23])=[O:22])[C:7]=3[NH:8][C:9]=2[CH:10]=1.O[CH:25]1[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]1>>[C:15]1([C:13]2[CH:12]=[C:11]([C:21]([NH2:23])=[O:22])[C:7]3[NH:8][C:9]4[CH:10]=[C:2]([O:1][CH:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:3]=[CH:4][C:5]=4[C:6]=3[N:14]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178513536HCID 178513536, compound

Product 1

HCID 66605107HCID 66605107, compound

Procedure

This was similarly prepared from 7-hydroxy-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxamide and tert-butyl 4-hydroxypiperidine-1-carboxylate. MS (ESI) m/z 387.1 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.35 (1H, br. s.), 8.57 (1H, s), 8.36 (1H, s), 8.28 (2H, d, J=7.02 Hz), 8.12 (1H, d, J=8.55 Hz), 7.84 (1H, s), 7.54 (2H, t, J=7.63 Hz), 7.42 (1H, t, J=7.32 Hz), 7.32 (1H, d, J=2.14 Hz), 6.91 (1H, dd, J=8.85, 2.14 Hz), 4.43-4.57 (1H, m), 3.05 (2H, ddd, J=12.67, 4.27, 4.12 Hz), 2.61-2.74 (2H, m), 1.98-2.11 (2H, m), 1.91 (3H, s), 1.50-1.68 (2H, m).

Sources & evidence

ORD record
ord-a1617c9503484d54b7a2f278dbd50334
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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