Triethylamine → HCID 59215841, compound

HRID 2074873Notes

Reaction equation

HRID 2074873 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-94efaf36048e4b078f9aeba0cbd74055
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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