Imidazole → [3-(tert-Butyl-silanoxy)-1-(S)-methyl-propyl]-carbamic acid benzyl ester

HRID 1046419Notes

Reaction equation

HRID 1046419 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@@H:11]([CH3:15])[CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])(C)C.N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@@H:11]([CH3:15])[CH2:12][CH2:13][O:14][SiH2:17][C:20]([CH3:23])([CH3:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66849810benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate

Product 1

HCID 131730925[3-(tert-Butyl-silanoxy)-1-(S)-methyl-propyl]-carbamic acid benzyl esterYield 114.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-Hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (8.02 g, 35.9 mmol) was taken up in DMF (75 mL). tert-Butyl-dimethylsilyl chloride (8.12 g, 53.9 mmol) was added to the solution followed by imidazole (4.15 g, 61.0 mmol). The reaction was stirred at rt and monitored by TLC. The reaction was determined to be complete at 1 h by TLC. The reaction was taken up in EtOAc (200 mL) and partitioned between 5% LiCl(aq) (200 mL). The aqueous was back extracted with EtOAc. The organics were combined and washed with 3×200 mL 5% LiCl(aq), and dried over Na2SO4. Solids were filtered and solvent removed under reduced pressure. [3-(tert-Butyl-silanoxy)-1-(S)-methyl-propyl]-carbamic acid benzyl ester (12.73 g, 100%) was isolated by silica gel chromatography as a white solid.

Workup

  1. custompartitioned between 5% LiCl(aq) (200 mL)
  2. extractionThe aqueous was back extracted with EtOAc
  3. washwashed with 3×200 mL 5% LiCl(aq)
  4. dry with materialdried over Na2SO4
  5. filtrationSolids were filtered
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-9dc55537fc694e00ac69cfb289acf66f
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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