1,4-Dioxane hydrochloride → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 717071Notes

Reaction equation

HRID 717071 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[C:25]([Si:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:11][CH2:10][CH2:9][NH:7][CH3:6])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 123833100HCID 123833100, compound

Product 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-methyl-carbamic acid tert-butyl ester (572 mg, 1.38 mmol) and 4M HCl/dioxane (3 mL) in CH2Cl2 (5 mL) were stirred at RT for 3 h. The reaction mixture was concentrated in vacuo and the crude material was purified by silica gel column chromatography, eluting with CH2Cl2 and increasing the polarity to 10% MeOH/CH2Cl2 to obtain [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-methyl-amine as a yellow solid (105 mg, 21%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude material was purified by silica gel column chromatography
  3. washeluting with CH2Cl2
  4. temperatureincreasing the polarity to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-bb845700b76a49c8881339bb9b801a41
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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