Triethylamine → HCID 69735169, compound

HRID 394525Notes

Reaction equation

HRID 394525 reaction equation
[CH2:1]([C:8]1([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22]([O:27][C@@H:28]([C:30]1[N:35]=[C:34](OS(C)(=O)=O)[CH:33]=[CH:32][N:31]=1)[CH3:29])(=[O:26])[CH2:23]CC>ClCCl>[C:22]([O:27][C@@H:28]([C:30]1[N:31]=[C:32]([N:11]2[CH2:12][CH2:13][C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)([OH:14])[CH2:9][CH2:10]2)[CH:33]=[CH:34][N:35]=1)[CH3:29])(=[O:26])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 981524-Benzyl-4-piperidinolHCID 54561222HCID 54561222, compound

Product 1

HCID 69735169HCID 69735169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzyl-4-hydroxypiperidine (0.95 g, 5.0 mmol) and triethylamine (0.51 g, 5.0 mmol) in dichloromethane (10 mL) was added (R)-1-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl butyrate (prepared according to the method of Preparation Eight, 123 g, 4.0 mmol) and stirred at ambient temperature for 18 h. The mixture was washed once with water, once with saturated aqueous sodium chloride and the organic layer was dried over sodium sulfate and filtered. The filtrate was evaporated to an oil which was purified by flash chromatography (95:5 dichloromethane:methanol) to give the title compound of Example 174, Step A as a viscous oil, 0.99 g (52%). 1H NMR (CDCl3, 300 MHz) δ 0.95 (t, 3H), 1.53 (d, 3H), 1.65-1.78 (m, 4H), 1.88 (m, 2H), 2.08 (m, 2H), 2.48 (t, 2H), 3.45 (m, 2H), 4.42 (br s, 1H), 5.68 (q, 1H), 6.41 (d, 1H), 7.30-7.48 (m, 5H), 8.18 (d, 1H); MS (CI) 384 (MH+).

Workup

  1. customprepared
  2. customaccording to the method of Preparation Eight, 123 g, 4.0 mmol) and
  3. washThe mixture was washed once with water, once with saturated aqueous sodium chloride
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated to an oil which
  7. customwas purified by flash chromatography (95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-a2cf5d10926748038562a1792285bd53
Source dataset
uspto-grants-2003_08
Patent number
US06602875B2

Reaction notes

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