Aluminium lithium hydride → HCID 69075874, compound

HRID 2110024Notes

Reaction equation

HRID 2110024 reaction equation
C[O:2][C:3]([C:5]1[CH:48]=[CH:47][C:8]2[N:9]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:10]([N:12]([CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=[CH:31][CH:30]=4)[CH2:24][CH2:23]3)[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][C:7]=2[CH:6]=1)=O.[H-].[Li+].[Al+3].[H-].[H-].[H-]>O1CCCC1>[C:29]1([CH2:28][N:25]2[CH2:24][CH2:23][CH:22]([CH2:21][N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:10]3[N:9]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:44])([CH3:45])[CH3:46])[C:8]4[CH:47]=[CH:48][C:5]([CH2:3][OH:2])=[CH:6][C:7]=4[N:11]=3)[CH2:27][CH2:26]2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 690756512-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

Product 1

HCID 69075874HCID 69075874, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (624 mg, 0.91 mmol) in anhydrous tetrahydrofuran (10 ml) under a nitrogen stream, aluminum lithium hydride (72.4 mg, 1.82 mmol) was added at 0° C., and the mixture was stirred for 2 hours. After then adding a saturated aqueous sodium sulfate solution, extraction was performed with ethyl acetate and then with dichloromethane. Each extract was washed with saturated brine, and then combined and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain [2-[(1-naphthalen-1-ylmethyl-piperidin -4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-5-yl]-methanol. The compound was identified by LC-MS.

Workup

  1. additionwas added at 0° C.
  2. additionAfter then adding
  3. extractiona saturated aqueous sodium sulfate solution, extraction
  4. washEach extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-60f78bdc023c4cc49ed65e3a39cefacf
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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