Hydrochloric Acid → HCID 59215763, compound

HRID 421238Notes

Reaction equation

HRID 421238 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C@@H:8]1[CH2:17][N:16]2[C@H:11]([CH2:12][O:13][CH2:14][CH2:15]2)[CH2:10][N:9]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(C)C.Cl>CO>[C:19]1([CH2:18][N:9]2[C@H:8]([CH2:7][OH:6])[CH2:17][N:16]3[C@H:11]([CH2:12][O:13][CH2:14][CH2:15]3)[CH2:10]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59215829HCID 59215829, compound

Product 1

HCID 59215763HCID 59215763, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-8-(phenylmethyl)octahydropyrazino[2,1-c][1,4]oxazine (D126, 276 mg, 0.73 mmol) in MeOH (24 ml), cooled to 0° C., was added dropwise 12 N HCl (1.4 mL). The reaction mixture was stirred for 2 hrs at r.t., then it was put in the freezer for 12 hrs. The reaction mixture was warmed-up to r.t., further HCl was added (0.7 ml) and the reaction mixture was stirred for 2 more hrs. The mixture was filtered on a SCX cartridge washing with methanol and then with 2M methanolic ammonia. The fractions eluted with ammonia were combined and evaporated to dryness to give the title compound as a colourless oil (150 mg, y=78%).

Workup

  1. waitit was put in the freezer for 12 hrs
  2. temperatureThe reaction mixture was warmed-up to r.t.
  3. stirringthe reaction mixture was stirred for 2 more hrs
  4. filtrationThe mixture was filtered on a SCX cartridge
  5. washwashing with methanol
  6. washThe fractions eluted with ammonia
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-499b9fa91076407cb819e6c075330fdf
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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