Triethylamine → HCID 68614182, compound

HRID 1753695Notes

Reaction equation

HRID 1753695 reaction equation
C(N(CC)CC)C.C([SiH](CC)CC)C.[CH2:15]([O:20][C:21]([N:23]1[C:27](=[O:28])[CH2:26][CH2:25][CH:24]1[C:29]([O:31]CC1C=CC=CC=1)=[O:30])=[O:22])[CH2:16][CH2:17][CH:18]=[CH2:19]>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:15]([O:20][C:21]([N:23]1[C:27](=[O:28])[CH2:26][CH2:25][CH:24]1[C:29]([OH:31])=[O:30])=[O:22])[CH2:16][CH2:17][CH:18]=[CH2:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 68613368HCID 68613368, compound

Product 1

HCID 68614182HCID 68614182, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, to a stirring solution of 240 mg of palladium acetate (1.1 mmol) in 20 mL of de-gassed dichloromethane, was added 460 uL of triethylamine (3.3 mmol), and 5.33 mL of triethylsilane (33 mmol). After stirring at rt for 15 min, 7.3 g of intermediate 17-2 in 25 mL of de-gassed dichloromethane was added in. The resulting solution was stirred at rt overnight. The reaction mixture was passed through a celite pad, and the filtrate was concentrated and purified by flash column chromatography using DCM/MeOH (v/v 9/1) as eluent, giving colorless oil 4.55 g (85%). LC-MS: m/z=240.1 (ES−).

Workup

  1. stirringThe resulting solution was stirred at rt overnight
  2. concentrationthe filtrate was concentrated
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-476ac76c5f4e4b88833b812ca9c75a5e
Source dataset
uspto-grants-2015_10
Patent number
US09163061B2

Reaction notes

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