Sodium hydride → 2-Chloro-5-(1-oxa-6-azaspiro[2.5]oct-6-ylmethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2298112Notes

Reaction equation

HRID 2298112 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]2)=[CH:26][C:11]=1[C:12]([NH:14][CH2:15][C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2)=[O:13]>CS(C)=O>[Cl:9][C:10]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[CH2:32][CH2:33][C:34]3([O:37][CH2:4]3)[CH2:35][CH2:36]2)=[CH:26][C:11]=1[C:12]([NH:14][CH2:15][C:16]12[CH2:23][CH:22]3[CH2:24][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH2:25]1)[CH2:17]2)=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 183815232-Chloro-5-[(4-oxo-1-piperidinyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 183815102-Chloro-5-(1-oxa-6-azaspiro[2.5]oct-6-ylmethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideYield 86.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To dimethylsulfoxide (2 ml) was added sodium hydride (0.033 g, 60 % in oil) at room temperature. The mixture was stirred for 5min. at this temperature and a solution of trimethylsulfoxonium iodide (0.178 g) in dimethylsulfoxide (2 ml) was added. After 30 min., 2-chloro-5-[(4-oxo-1-piperidinyl)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.28 g, Example 83a) in dimethylsulfoxide (2 ml) was added and the reaction stirred at room temperature for 3 h before being quenched with ice/water (20 ml). The mixture was extracted three times with ethyl acetate, the combined organic layers washed with brine and dried over magnesium sulfate. The crude material was purified on silica gel, eluting with ethyl acetate to afford the subtitle compound as a white foam (0.25 g).

Workup

  1. waitAfter 30 min.
  2. stirringthe reaction stirred at room temperature for 3 h
  3. custombefore being quenched with ice/water (20 ml)
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. washthe combined organic layers washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe crude material was purified on silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-139e4676082a4756a494684f3f19c2e7
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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