Methanol → HCID 68689713, compound

HRID 1159111Notes

Reaction equation

HRID 1159111 reaction equation
[CH2:1]([N:8]1[CH2:24][CH2:23][N:11]2[C:12](=[O:22])[C:13]3[C:14]([CH3:21])=[CH:15][CH:16]=[C:17]([OH:20])[C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[Br-:27].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[CH2:1]([N:8]1[CH2:24][CH2:23][N:11]2[C:12](=[O:22])[C:13]3[C:14]([CH3:21])=[CH:15][C:16]([Br:27])=[C:17]([OH:20])[C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23500184Tetra-n-butylammonium tribromide2×HCID 68688362HCID 68688362, compound

Product 1

HCID 68689713HCID 68689713, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-2-benzyl-7-methyl-10-hydroxy-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (190 mg, 0.59 mmol) in dry CH2Cl2:methanol (4:2 mL), tetrabutylammonium tribromide (331 mg, 0.68 mmol) was added. The reaction was stirred for 1 h under Argon added more tetrabutylammonium tribromide (45 mg, 0.09 mmol). After 20 min removed solvent in rotavap and then diluted with dichloromethane (100 mL), washed with 5% Na2S2O3 (10 mL), saturated NaHCO3 (10 mL) and brine (15 mL). The organic layer was dried over MgSO4, and conc in vacuo and purified by prep TLC (SiO2, 95:5, CH2Cl2:MeOH) to yield 86 mg (36%) of the product as a faint brown oil. MS (ESI) 401, 403 (M+H).

Workup

  1. customAfter 20 min removed solvent in rotavap
  2. additiondiluted with dichloromethane (100 mL)
  3. washwashed with 5% Na2S2O3 (10 mL), saturated NaHCO3 (10 mL) and brine (15 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customconc in vacuo and purified by prep TLC (SiO2, 95:5, CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-8ff7e04785584f1389875cd11c28ac17
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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