Triethylsilane → HCID 117690149, compound

HRID 1502086Notes

Reaction equation

HRID 1502086 reaction equation
O[CH2:2][C@H:3]1[N:8]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)=[O:11])[CH2:7][CH2:6][N:5]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:4]1.C([SiH](CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>[N+:18]([C:14]1[CH:13]=[C:12]([CH:10]2[O:11][CH2:2][C@@H:3]3[CH2:4][N:5]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:6][CH2:7][N:8]3[CH2:9]2)[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

7

Reactant 3

HCID 12052TriethylsilaneHCID 90495Di-tert-butyl dicarbonateHCID 89618826HCID 89618826, compound

Product 1

HCID 117690149HCID 117690149, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

(S)-tert-butyl 3-(hydroxymethyl)-4-(2-(3-nitrophenyl)-2-oxoethyl)piperazine-1-carboxylate (1.5 g, 3.95 mmol) was dissolved in mixture of DCM (10 mL)/TFA (5 ml) then added triethylsilane (3.16 mL, 19.8 mmol) and stirred at room temperature overnight. The reaction mixture was concentrated. The residue was dissolved in DCM (15 mL) with saturated aqueous NaHCO3 (15 ml) and di-tert-butyl dicarbonate (2.157 g, 9.88 mmol) was added then stirred for 2 hrs. The reaction was extracted with DCM (2×). The combined DCM was washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The product was chromatographed through 120 g ISCO Redi-sep column and eluted with 10-70% ethyl acetate/hexane to yield the title compound; the product was almost exclusively the trans isomer.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwas added
  3. extractionThe reaction was extracted with DCM (2×)
  4. washThe combined DCM was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe product was chromatographed through 120 g ISCO Redi-sep column
  9. washeluted with 10-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-02d0cc28acd14f5ca1843fce36764ec6
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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