Pyridine → 2-(trimethylsilyl)ethyl (2R,3S)-3-amino-4-(tetrahydro-2H-pyran-4-yl)-2-(trimethylsilyloxy)butyl(methyl)carbamate

HRID 253586Notes

Reaction equation

HRID 253586 reaction equation
[NH2:1][C@@H:2]([CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C@H:3]([OH:16])[CH2:4][N:5]([CH3:15])[C:6](=[O:14])[O:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11].N1C=CC=CC=1.[Si:30](Cl)([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[NH2:1][C@@H:2]([CH2:17][CH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[C@H:3]([O:16][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH2:4][N:5]([CH3:15])[C:6](=[O:14])[O:7][CH2:8][CH2:9][Si:10]([CH3:12])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 66861533HCID 66861533, compound

Product 1

HCID 668613742-(trimethylsilyl)ethyl (2R,3S)-3-amino-4-(tetrahydro-2H-pyran-4-yl)-2-(trimethylsilyloxy)butyl(methyl)carbamateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL flask was charged with 2-(trimethylsilyl)ethyl (2R,3S)-3-amino-2-hydroxy-4-(tetrahydro-2H-pyran-4-yl)butyl(methyl)carbamate (100 mg, 0.29 mmol) dissolved in THF (10 mL), pyridine (68 mg, 0.87 mmol) was added at 0° C. Me3SiCl (94 mg, 0.87 mmol) was added and the mixture was stirred for 2 h at rt. The mixture was quenched with 1% aq HCl and extracted with EtOAc (3×15 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography to give 2-(trimethylsilyl)ethyl (2R,3S)-3-amino-4-(tetrahydro-2H-pyran-4-yl)-2-(trimethylsilyloxy)butyl(methyl)carbamate (110 mg, 92%)

Workup

  1. customThe mixture was quenched with 1% aq HCl
  2. extractionextracted with EtOAc (3×15 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-8c3c66ee077e40499fb6a7a9c8c082b1
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

Loading…