Piperidin-4-ol → HCID 21060062, compound

HRID 720292Notes

Reaction equation

HRID 720292 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[OH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:30]2[CH2:31][CH2:32][CH:27]([OH:26])[CH2:28][CH2:29]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 21060065HCID 21060065, compound

Product 1

HCID 21060062HCID 21060062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-Benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.725 g, 2 mmol) and 4-hydroxypiperidine (1 g, 10 mmol) in THF (20 mL) was stirred for 16 h at ambient temperature. Then, the reaction mixture was taken up in EtOAC (100 mL), washed with 1N aq HCl (2×10 mL) and brine (10 mL). The organic phase was dried (Na2SO4), filtered and concentrated to give the desired product as a pale yellow paste (0.608 g, 79%) which was used in the subsequent reaction without further purification. 1H NMR (500 MHz, CDCl3) δ: 7.46 (d, J=7.0 Hz, 2H), 7.36–7.28 (m, 3H), 5.14 (s, 2H), 4.30 (q, J=7.0 Hz, 2H), 3.92–3.87 (m, 1H), 3.50 (s, 3H), 3.44–3.39 (m, 2H), 3.01–2.95 (m, 2H), 2.79 (br s, 1H), 2.02–1.98 (m, 2H), 1.71–1.64 (m, 2H), 1.28 (t, J=7.0 Hz, 3H). LRMS (M+H) calcd for C20H26N3O5: 388.44. found: 388.20

Workup

  1. washwashed with 1N aq HCl (2×10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-30544422b2524efebcda161a5a03da27
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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