Hydrochloric Acid → HCID 59215834, compound

HRID 2074887Notes

Reaction equation

HRID 2074887 reaction equation
[OH:1][CH2:2][C@H:3]1[C:12](=O)[N:11]2[CH:6]([CH2:7][O:8][CH2:9][CH2:10]2)[C:5](=O)[NH:4]1.Cl>CO>[CH2:7]1[CH:6]2[CH2:5][NH:4][C@@H:3]([CH2:2][OH:1])[CH2:12][N:11]2[CH2:10][CH2:9][O:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59215806HCID 59215806, compound

Product 1

HCID 59215834HCID 59215834, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(7S)-7-(hydroxymethyl)hexahydropyrazino[2,1-c][1,4]oxazine-6,9-dione (D130, 151 mg, 0.75 mmol) was suspended in 1M borane THF complex solution (7.5 mL) and heated at reflux for 24 hours. Checked by MS, which showed only the product at m/z=173 (M+1). The reaction was cooled to 0° C., MeOH (5 mL) added dropwise followed by conc.HCl solution (1 mL). The resulting mixture was heated at 50° C. for 4 hours. The solvent was removed and the residue loaded on a SCX column, washed with MeOH before eluting the compound with 1M NH3 in MeOH. Solvent evaporated under reduced pressure to afford the title compound as a colourless oil (125 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. temperatureThe resulting mixture was heated at 50° C. for 4 hours
  4. customThe solvent was removed
  5. washwashed with MeOH
  6. washbefore eluting the compound with 1M NH3 in MeOH
  7. customSolvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-7ba555db65dd40d697fa996793a3145e
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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