Sodium hydride → HCID 68912174, compound

HRID 732659Notes

Reaction equation

HRID 732659 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[CH:10]([C:14]([O:16]CC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:25]([Si:29]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)Cl)([CH3:28])([CH3:27])[CH3:26].C(N1CC(C)C(CO)C1)C1C=CC=CC=1.[H-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[CH:10]([CH2:14][O:16][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 94078tert-ButyldiphenylchlorosilaneHCID 18713552HCID 18713552, compoundHCID 21226445Aluminium lithium hydrideHCID 23397015HCID 23397015, compound

Product 1

HCID 68912174HCID 68912174, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-benzyl-4-methylpyrrolidine-3-carboxylate synthesized in accordance with the method of International Patent Publication WO 2000/15611 was reduced with lithium aluminum hydride in accordance with the method of International Patent Publication WO 2000/59502. Tert-butyldiphenylchlorosilane was added to a THF solution of the thus obtained (1-benzyl-4-methylpyrrolidin-3-yl)methanol, sodium hydride was added thereto under ice-cooling, and the mixture was stirred at room temperature for 2Hours. Thereafter, its work-up and purification were carried out in the standard method to obtain 1-benzyl-3-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-methylpyrrolidine. AP: 444.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. customThereafter, its work-up and purification

Sources & evidence

ORD record
ord-b3e557903c4c46179d1678bea5bac605
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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