Triethylamine → HCID 59215853, compound

HRID 2074869Notes

Reaction equation

HRID 2074869 reaction equation
[CH2:1]1[NH:6][C@@H:5]([CH2:7][OH:8])[CH2:4][N:3]2[CH2:9][CH2:10][CH2:11][C@@H:2]12.C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>ClCCl>[CH3:23][C:22]([Si:19]([CH3:21])([CH3:20])[O:8][CH2:7][C@@H:5]1[CH2:4][N:3]2[CH2:9][CH2:10][CH2:11][C@H:2]2[CH2:1][NH:6]1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11805009(3R,8aS)-Octahydropyrrolo[1,2-a]pyrazine-3-methanol

Product 1

HCID 59215853HCID 59215853, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3R,8aS)-octahydropyrrolo[1,2-a]pyrazin-3-ylmethanol (Tetrahedron Asymmetry, 1996, 7(7), 1999-2005) (531.5 mg, 3.39 mmol) in 20 mL of dichloromethane was added triethylamine (1.423 mL, 10.17 mmol) and tert-butyldimethylsilyl chloride (1.026 g, 6.78 mmol). The solution was stirred at room temperature for 2 days. The reaction was diluted with dichloromethane and extracted with sat. NaHCO3 and brine. The product was isolated by flash chromatography (dichloromethane to dichloromethane: MeOH 99:1 to 90:10), obtaining 157 mg of the title compound.

Workup

  1. extractionextracted with sat. NaHCO3 and brine
  2. customThe product was isolated by flash chromatography (dichloromethane to dichloromethane: MeOH 99:1 to 90:10)

Sources & evidence

ORD record
ord-4a6465f4bd3148fda6b332031df04a97
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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