Sodium Sulfate → HCID 178519374, compound

HRID 2110020Notes

Reaction equation

HRID 2110020 reaction equation
C[O:2][C:3]([C:5]1[CH:39]=[CH:38][C:8]2[N:9](C(OC(C)(C)C)=O)[C:10]([NH:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH:24]=[CH:23][CH:22]=4)[CH2:16][CH2:15]3)=[N:11][C:7]=2[CH:6]=1)=O.[H-].[Li+].[Al+3].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:21]1([CH2:20][N:17]2[CH2:16][CH2:15][CH:14]([CH2:13][NH:12][C:10]3[NH:9][C:8]4[CH:38]=[CH:39][C:5]([CH2:3][OH:2])=[CH:6][C:7]=4[N:11]=3)[CH2:19][CH2:18]2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 69075759HCID 69075759, compound

Product 1

HCID 178519374HCID 178519374, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-benzimidazole-1,5-dicarboxylic acid 1-tert-butyl ester 5-methyl ester (940 mg, 1.78 mmol) in dry tetrahydrofuran (18 ml) under a nitrogen stream, aluminum lithium hydride (135 mg, 3.56 mmol) was added at 0° C., and the mixture was stirred for 3 hours. Saturated aqueous sodium sulfate was added, and then the solvent was distilled off under reduced pressure. Since the residue contained water, it was dissolved in ethyl acetate and washed with saturated brine, and the solvent was then distilled off under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (dichloromethane/methanol/TEA=90/5/5) to obtain {2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazol-5-yl-}-methanol.

Workup

  1. additionwas added at 0° C.
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed with saturated brine
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customto obtain a residue
  7. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol/TEA=90/5/5)

Sources & evidence

ORD record
ord-b0503c52b12d43fea942d94fccc7c1e6
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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