Triethylamine → HCID 59215841, compound

HRID 421226Notes

Reaction equation

HRID 421226 reaction equation
[CH2:1]1[NH:6][C@@H:5]([CH2:7][OH:8])[CH2:4][N:3]2[CH2:9][CH2:10][NH:11][CH2:12][CH:2]12.CCN(CC)CC.[CH3:20][C:21]([Si:24]([CH3:40])([CH3:39])OCC1CN2C(CS(=O)(=O)CC2)CN1)([CH3:23])[CH3:22]>ClCCl>[CH3:20][C:21]([Si:24]([CH3:40])([CH3:39])[O:8][CH2:7][C@H:5]1[CH2:4][N:3]2[CH2:9][CH2:10][NH:11][CH2:12][CH:2]2[CH2:1][NH:6]1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59215772HCID 59215772, compoundHCID 66669046HCID 66669046, compound

Product 1

HCID 59215841HCID 59215841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The starting (3R)-octahydro-2H-pyrazino[1,2-a]pyrazin-3-ylmethanol (D89, 528 mg, 3.08 mmol) was dissolved in 20 mL of dichloromethane and treated with Et3N (1.29 mL, 9.25 mmol) and TDBMSCl (929.5 mg, 6.17 mmol). The reaction was stirred at room temperature overnight and then for additional 24 h. It was checked by UPLC/MS, which showed conversion to product: peak at 0.47 min, m/z=286 (M+1), 172 (M-TBDMS+1). The crude was purified by flash chromatography (silica, CH2Cl2: (0.5 M NH3 in MeOH) 98:2 to 85:15). The residue obtained evaporating the fractions containing the product was dissolved in dichloromethane:MeOH 90:10 and the insoluble material was filtered away. The solution was evaporated to give 638 mg of the target product.

Workup

  1. waitfor additional 24 h
  2. waitpeak at 0.47 min
  3. customThe crude was purified by flash chromatography (silica, CH2Cl2: (0.5 M NH3 in MeOH) 98:2 to 85:15)
  4. customThe residue obtained
  5. customevaporating the fractions
  6. additioncontaining the product
  7. dissolutionwas dissolved in dichloromethane:MeOH 90:10
  8. filtrationthe insoluble material was filtered away
  9. customThe solution was evaporated

Sources & evidence

ORD record
ord-d2f29a22d0ab4a5e918966ce2de9c449
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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