Hydrochloric Acid → HCID 59215772, compound
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][C@@H:3]([CH2:2][OH:1])[CH2:8][N:7]2[CH2:10][CH2:11][NH:12][CH2:13][CH:6]12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 and (3S,9aR or 9aS)-3-(hydroxymethyl)tetrahydro-2H-pyrazino[1,2-a]pyrazine-1,4(3H,6H)-dione (D83, Diastereoisomer 1 plus D84,Diastereoisomer 2, 976 mg, 4.9 mmol) was added 1M BH3-THF solution (49 mL) under nitrogen and the reaction was brought to reflux (80° C.) overnight. The reaction flask was cooled to 0° C. and treated with 25 mL of MeOH. Conc. HCl was added and the resulting solution was heated to 60° C. for 5 h. The reaction was checked by direct MS (m/z=184 (M+BH3) ). The reaction mixture was purified by SCX, obtaining 528 mg of product.
Workup
- temperatureThe reaction flask was cooled to 0° C.
- temperaturethe resulting solution was heated to 60° C. for 5 h
- customThe reaction mixture was purified by SCX
Sources & evidence
- ORD record
- ord-fbc7e98f07ec4f23916acff85d7342d3
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683056B2
Reaction notes
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