Imidazole → 5-[4-(Tert-butyldimethylsilyloxy)methylpiperidinomethyl]-1-(tert-butoxycarbonyl)indole

HRID 20987Notes

Reaction equation

HRID 20987 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:14]=[CH:13]3)[CH2:5][CH2:4]1.N1C=CN=C1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>CN(C=O)C>[Si:31]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:14]=[CH:13]3)[CH2:5][CH2:4]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68492881HCID 68492881, compound

Product 1

HCID 684921525-[4-(Tert-butyldimethylsilyloxy)methylpiperidinomethyl]-1-(tert-butoxycarbonyl)indoleYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Reference Example 18, 5-(4-hydroxymethylpiperidinomethyl)-1-(tert-butoxycarbonyl)indole (2.85 g, 8.27 mmol) was dissolved in DMF (50 mL), and the solution was treated with imidazole (619 mg, 9.09 mmol and tert-butyldimethylsilyl chloride (1.37 g, 9.09 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain 5-[4-(tert-butyldimethylsilyloxy)methylpiperidinomethyl]-1-(tert-butoxycarbonyl)indole (2.90 g, yield 76%).

Workup

  1. customfollowed by purification by flash column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-83be30e81b4f4e8e9884b6724877cc41
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

Loading…