Hydrochloric Acid → HCID 72533145, compound

HRID 2074870Notes

Reaction equation

HRID 2074870 reaction equation
[OH:1][CH2:2][CH:3]1[C:8](=O)[N:7]2[CH2:10][CH2:11][NH:12][CH2:13][CH:6]2[C:5](=O)[NH:4]1.B.C1COCC1.Cl>CO>[CH2:5]1[NH:4][CH:3]([CH2:2][OH:1])[CH2:8][N:7]2[CH2:10][CH2:11][NH:12][CH2:13][CH:6]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 72533144HCID 72533144, compound

Product 1

HCID 72533145HCID 72533145, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a flask containing (3S,9aS or 9aR)-3-(hydroxymethyl)tetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione (D83, 217 mg) was added 1M BH3-THF solution (10.9 mL) and the reaction was brought to reflux (80° C.) overnight. The reaction flask was cooled to 0° C. and treated with 20 mL of MeOH and conc. HCl (2.5 mL). The resulting solution was heated to 60° C. for 4 h. The reaction was checked by direct MS (m/z=172 (M+1), 184 (M+BH3)). The reaction mixture was purified by SCX, obtaining 174 mg of the title compound.

Workup

  1. temperatureThe reaction flask was cooled to 0° C.
  2. temperatureThe resulting solution was heated to 60° C. for 4 h
  3. customThe reaction mixture was purified by SCX

Sources & evidence

ORD record
ord-4992de8312d14c57b75429a3b4f952a6
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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