Imidazole → HCID 123833100, compound

HRID 717070Notes

Reaction equation

HRID 717070 reaction equation
[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][OH:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Si:13](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CN=C1>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][O:11][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 123833100HCID 123833100, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(2-Hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (400 mg, 2.28 mmol), TBDPS chloride (593 μL, 2.28 mmol) and imidazole (342 mg, 5.02 mmol) in DMF (2 mL) were stirred at RT for 12 h. The reaction mixture was diluted with brine and extracted with CH2Cl2. The combined organics were passed through a phase separation cartridge and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with isohexane and increasing the polarity to 50% EtOAc/isohexane to obtain [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-methyl-carbamic acid tert-butyl ester as a colourless oil (572 mg, 61%).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe combined organics were passed through a phase separation cartridge
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with isohexane
  6. temperatureincreasing the polarity to 50% EtOAc/isohexane

Sources & evidence

ORD record
ord-6cee573f13894352bec7885d127c378c
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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