Hydrochloric Acid → HCID 11450351, compound

HRID 1296251Notes

Reaction equation

HRID 1296251 reaction equation
C(OC([N:8]1[CH2:29][CH2:28][N:11]2[C:12](=[O:27])[C:13]3[C:18]([CH:10]2[CH2:9]1)=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)(C)(C)C.Cl>>[CH2:20]([O:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[C:12](=[O:27])[N:11]1[CH2:28][CH2:29][NH:8][CH2:9][CH:10]12)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68690796HCID 68690796, compound

Product 1

HCID 11450351HCID 11450351, compound

Procedure

To N-(t-butoxycarbonyl)-(±)-1,3,4,10b-tetrahydro-7-benzyloxy-pyrazino[2,1-a]isoindol-6(2H)-one (31 mg, 0.08 mmol) was added concentrated aqueous hydrogen chloride (1 mL). After 5 min, the solution was concentrated, treated with saturated aqueous ammonium chloride, and reconcentrated. The resulting mixture was purified via radial chromatography (8% methanol in dichloromethane containing 2% ammonium hydroxide) to give (±)-1,3,4,10b-tetrahydro-7-benzyloxy-pyrazino[2,1-a]isoindol-6(2H)-one. This material was treated with aqueous hydrogen chloride (1N), concentrated, diluted with water, and lyopholized to give the desired product as an off-white solid (19 mg, 72%). MS (ESI) 295.3 (M−Cl).

Workup

  1. concentrationthe solution was concentrated
  2. additiontreated with saturated aqueous ammonium chloride
  3. customThe resulting mixture was purified via radial chromatography (8% methanol in dichloromethane containing 2% ammonium hydroxide)

Sources & evidence

ORD record
ord-cffc1fb49bb34130b5954b864fa14df4
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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