Dichloromethane → HCID 66800148, compound

HRID 1528292Notes

Reaction equation

HRID 1528292 reaction equation
C(N(CC)CC)C.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].C(Cl)Cl.[N:19]1([CH2:29][CH2:30][OH:31])[C@H:28]2[C@@H:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[NH:22][CH2:21][CH2:20]1>O>[Si:8]([O:31][CH2:30][CH2:29][N:19]1[C@H:28]2[C@@H:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[NH:22][CH2:21][CH2:20]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 86697504HCID 86697504, compound

Product 1

HCID 66800148HCID 66800148, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (4.61 mL, 33.0 mmol) and subsequently tert-butyldimethylsilyl chloride (4.27 g, 28.3 mmol) were added to a methylene chloride (40 mL) solution of 2-(trans -decahydroquinoxalin-1-yl)ethanol (1.74 g, 9.44 mmol) with ice-cooling and stirring, and the mixture was stirred overnight at room temperature. To the reaction mixture, water (100 mL) was added to terminate the reaction. The product was extracted with methylene chloride (100 mL). The organic layer was washed with water twice and with saturated saline once, then dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride/methanol) to obtain trans-1-[2-(tert-butyldimethylsilyloxy)ethyl]decahydroquinoxaline (2.00 g, yield: 71%) in a light brown oil form.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionThe product was extracted with methylene chloride (100 mL)
  6. washThe organic layer was washed with water twice
  7. dry with materialwith saturated saline once, then dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-16a11ed3f5eb4fe2b9a5d114a083dd4f
Source dataset
uspto-grants-2015_07
Patent number
US09090572B2

Reaction notes

Loading…