Triethylamine → HCID 57235283, compound

HRID 1384310Notes

Reaction equation

HRID 1384310 reaction equation
Br[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([CH3:25])[C:7]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[C:8]([CH3:13])[CH:9]=2)[O:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2([OH:39])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1.C(N(CC)CC)C>C(#N)C>[CH3:13][C:8]1[CH:9]=[C:10]2[C:5](=[C:6]([CH3:25])[C:7]=1[OH:14])[O:4][CH2:3][C@@H:2]([N:36]1[CH2:35][CH2:34][C:33]([C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)([OH:39])[CH2:38][CH2:37]1)[C@H:11]2[OH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 774974-(4-Fluorophenyl)piperidin-4-olHCID 21186608HCID 21186608, compound

Product 1

HCID 57235283HCID 57235283, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-bromo-6,8-dimethyl-7-triisopropylsilyloxychromen-4-one (the compound of Example 19, 0.23 g, 0.54 mmol), 4-(4-fluorophenyl)-4-hydroxypiperidine (0.22 g, 1.12 mmol) and triethylamine (0.3 mL, 2.15 mmol) in acetonitrile (15 mL) was stirred over the weekend at ambient temperature. The precipitate which formed was collected and rinsed with water and ether. This solid was flash chromatographed on silica gel (1×4 inches packed in hexane) with elution proceeding as follows: 10% ethyl acetate/hexane (100 mL), nil; 25% ethyl acetate/hexane (200 mL), 0.065 g (22%) 6,8-dimethyl-7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one which had: mp 226.5-227° C. Analysis calculated for C31H42FNO4Si: C, 68.98; H, 7.84; N, 2.59. Found: C, 69.00; H, 7.94; N, 2.37. This product was identical to the product isolated in the first step of example 19 and was converted to the title product following the procedure of example 19.

Workup

  1. customThe precipitate which formed
  2. customwas collected
  3. washrinsed with water and ether
  4. customchromatographed on silica gel (1×4 inches packed in hexane) with elution proceeding
  5. customisolated in the first step of example 19

Sources & evidence

ORD record
ord-024ca1665bd440f08957c9d4f1ff9eb7
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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