Tetrahydrofuran → HCID 68509007, compound

HRID 1716569Notes

Reaction equation

HRID 1716569 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[N:12]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]2CCC(O)=O)[C:11]2[CH:31]=[CH:32][C:33]([CH3:35])=[CH:34][C:10]=2[N:9]=1.C1C[O:39][CH2:38]C1>>[CH3:7][C:8]1[N:12]([C@@H:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][C@H:14]2[CH2:38][OH:39])[C:11]2[CH:31]=[CH:32][C:33]([CH3:35])=[CH:34][C:10]=2[N:9]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 68510132HCID 68510132, compound

Product 1

HCID 68509007HCID 68509007, compound

Procedure

Lithium aluminum hydride (76 mg; 2 mmol) was added to a stirring solution of 4-(2,5-dimethylbenzimidazol-1-yl)-3-carboxyethyl-N-Boc piperidine (310 mg; 0.77 mmol) in THF (5 mL) under Ar at 0° C. After one hour, Na2SO4 decahydrate (500 mg; 1.55 mmol) was added carefully portionwise. The reaction mixture was stirred 2 h and the grey solid that formed during this time was removed by filtration through Celite®. Volatiles were removed under reduced pressure and the product racemic trans-4-(2,5-dimethylbenzimidazol-1-yl)-3-hydroxymethyl-N-Boc piperidine was isolated by flash chromatography (258 mg; 93%) as a white powder.

Workup

  1. customthe grey solid that formed during this time
  2. customwas removed by filtration through Celite®
  3. customVolatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-7f49f1ec92bf416bbb298e33157f422c
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

Loading…