Chlorotrimethylsilane → HCID 59702321, compound

HRID 902563Notes

Reaction equation

HRID 902563 reaction equation
C([BH3-])#N.[Na+].C[Si](Cl)(C)C.[CH2:10]([S:12][C:13]1[N:14]([CH3:31])[N:15]=[C:16]2[C:21]=1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30])[CH3:11].[OH-:32].[Na+].C1C[O:37]CC1>>[CH2:10]([S:12]([C:13]1[N:14]([CH3:31])[N:15]=[C:16]2[C:21]=1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]1[C:23]([CH3:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28])(=[O:37])=[O:32])[CH3:11]

Participants

6

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 59702301HCID 59702301, compound

Product 1

HCID 59702321HCID 59702321, compoundYield 41%

Procedure

A mixture of sodium cyanoborohydride (0.276 g, 4.39 mmol), 5 mL of THF, and TMSCl (0.56 mL, 4.4 mmol) was stirred for 10 m, then 45 (0.780 g, 3.67 mmol) in 10 mL of THF was slowly added. The mixture was stirred for 1 h, then 15 mL of a 2 M aqueous NaOH solution were added. The mixture was extracted with 40 mL of diethyl ether, and the organic layer was washed with two 20 mL portions of a saturated aqueous NaCl solution, dried over Na2SO4, filtered, and concentrated. Column chromatography (0→20% EtOAc/hexanes) afforded N′-cyclopropylmethyl-N-ethyl-hydrazinecarboxylic acid tert-butyl ester (46; 0.323 g; 41%).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. extractionThe mixture was extracted with 40 mL of diethyl ether
  3. washthe organic layer was washed with two 20 mL portions of a saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-706c77108abc4968a0a364fa7d379aa7
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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