Hydrochloric Acid → HCID 11383152, compound

HRID 1296232Notes

Reaction equation

HRID 1296232 reaction equation
C(OC([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([Br:19])=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=O)(C)(C)C.[ClH:27]>C(OCC)C>[ClH:27].[Br:19][C:16]1[CH:17]=[C:18]2[C:13]([C:12](=[O:24])[N:11]3[CH2:25][CH2:26][NH:8][CH2:9][C@H:10]32)=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 16115648HCID 16115648, compound

Product 1

HCID 11383152HCID 11383152, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-bromo-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one from Step A (105 mg, 0.24 mmol) was added diethyl ether (2 nL) and saturated aqueous hydrochloric acid (1 mL). After 15 min of stirring, the reaction was concentrated and treated with saturated aqueous ammonium hydroxide (2 nL). The solution was concentrated to dryness and the resulting residue was purified by radial chromatography (2% ammonium hydroxide in 4% methanol in dichloromethane) to give a clear residue. The residue was treated with 1N aqueous hydrogen chloride and lyophilized to afford the desired product (33 mg, 37%) as an off-white solid. MS (ESI) 335.2, 337.2 (M−Cl).

Workup

  1. concentrationthe reaction was concentrated
  2. additiontreated with saturated aqueous ammonium hydroxide (2 nL)
  3. concentrationThe solution was concentrated to dryness
  4. customthe resulting residue was purified by radial chromatography (2% ammonium hydroxide in 4% methanol in dichloromethane)
  5. customto give a clear residue

Sources & evidence

ORD record
ord-d16eb320fd8645dd97e62efb5c6453e5
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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