Borane;tetrahydrofuran → (3R)-3-methyloctahydro-2H-pyrazino[1,2-a]pyrazine

HRID 421230Notes

Reaction equation

HRID 421230 reaction equation
[CH3:1][C@@H:2]1[C:7](=O)[N:6]2[CH2:9][CH2:10][NH:11][CH2:12][CH:5]2[C:4](=O)[NH:3]1.B.C1COCC1>Cl>[CH3:1][C@@H:2]1[CH2:7][N:6]2[CH2:9][CH2:10][NH:11][CH2:12][CH:5]2[CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 59215897(3R)-3-methyltetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione

Product 1

HCID 59215786(3R)-3-methyloctahydro-2H-pyrazino[1,2-a]pyrazineYield 81.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a flask containing (3R)-3-methyltetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione (D98, 353 mg, 1.927 mmol) was added 1M BH3-THF solution (20 mL) and it was heated to reflux for 20 h. MS analysis: m/z=156 (M+1 of the target product). To the reaction were added at 0° C. 10 mL of 6M HCl and it was heated to 90° C. for 20 h. The reaction mixture was purified by SCX, obtaining 243 mg of the target compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. additionTo the reaction were added at 0° C
  4. customThe reaction mixture was purified by SCX

Sources & evidence

ORD record
ord-b0628188c43b484abda9898aea366d02
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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