Imidazole → (2S,3S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-butan-2-ol

HRID 538920Notes

Reaction equation

HRID 538920 reaction equation
[NH2:1][C@@H:2]([CH2:6][OH:7])[C@H:3]([CH3:5])[OH:4].N1C=CN=C1.[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>CN(C=O)C.CCOC(C)=O>[NH2:1][C@@H:2]([CH2:6][O:7][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)[C@@H:3]([OH:4])[CH3:5]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 7020320(2S,3S)-2-Amino-1,3-butanediol

Product 1

HCID 89766699(2S,3S)-3-Amino-4-(tert-butyl-diphenyl-silanyloxy)-butan-2-olYield 49.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

D-threoninol (2 g, 19.02 mmol) was dissolved in DMF (15 ml), treated with imidazole (3.89 g, 57.1 mmol) and stirred at RT for 5 min. Then, TBDPS-Cl (5.13 ml, 19.97 mmol) was added dropwise to the reaction solution under argon. The reaction solution was stirred for 16H at RT. Then it was diluted in EtOAc and washed twice with saturated NaHCO3 solution and once with brine. Organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 100%→0% heptane.) to give the title compound (3.21 g, 47%). tR: 0.98 min (LC-MS 1); ESI-MS: 344.3 [M+H]+ (LC-MS 1).

Workup

  1. stirringThe reaction solution was stirred for 16H at RT
  2. washwashed twice with saturated NaHCO3 solution and once with brine
  3. dry with materialOrganic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (heptane/EtOAc: 100%→0% heptane.)

Sources & evidence

ORD record
ord-f23a4fb4626c40d28d249faee7c184cf
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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