Acetyl chloride → HCID 72533160, compound

HRID 421224Notes

Reaction equation

HRID 421224 reaction equation
[CH3:1][C:2]([Si:5]([CH2:8][CH:9]1[CH2:14][N:13]2[CH2:15][CH2:16][NH:17][CH2:18][CH:12]2[CH2:11][NH:10]1)([CH3:7])[CH3:6])([CH3:4])[CH3:3].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[C:26]([N:17]1[CH2:16][CH2:15][N:13]2[CH2:14][CH:9]([CH2:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[NH:10][CH2:11][CH:12]2[CH2:18]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 72533163HCID 72533163, compound

Product 1

HCID 72533160HCID 72533160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of the (3R,9aS or 9aR)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]methyl}octahydro-2H-pyrazino[1,2-a]pyrazine (D86, 217 mg) in 9 mL of dichloromethane was added triethylamine (212 μL) and it was brought to −10° C. A solution of acetyl chloride (54 μL) in 2 mL of dichloromethane was added dropwise. After 15 min the reaction was quenched by addition of MeOH. The crude was purified by flash chromatography (silica, CH2Cl2 to CH2Cl2: (0.5 M NH3 in MeOH) 95:5). The sample thus obtained was dissolved in CH2Cl2 and extracted with sat. NaHCO3. The organics were dried and the solvent removed, leading to the title compound (128 mg).

Workup

  1. customwas brought to −10° C
  2. customAfter 15 min the reaction was quenched by addition of MeOH
  3. customThe crude was purified by flash chromatography (silica, CH2Cl2 to CH2Cl2: (0.5 M NH3 in MeOH) 95:5)
  4. customThe sample thus obtained
  5. extractionextracted with sat. NaHCO3
  6. customThe organics were dried
  7. customthe solvent removed

Sources & evidence

ORD record
ord-f506a38857c1419b890949c2532f4709
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

Loading…