Sodium methanethiolate → HCID 68687732, compound

HRID 1159044Notes

Reaction equation

HRID 1159044 reaction equation
[C:1]([O:5][C:6]([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)=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][S-:28].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([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]([S:28][CH3:27])=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 16115648HCID 16115648, compound

Product 1

HCID 68687732HCID 68687732, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-bromo-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (56 mg, 0.13 mmol) in dry DMF (1 mL) at 60° C. was added sodium methanethiolate (9.9 mg, 0.14 mmol). The reaction was heated to reflux for 30 min and then cooled to room temperature. The reaction was quenched with 1M aq. NaOH and extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a yellow oil. The oil was purified by flash chromatography (silica gel, 0-33% EtOAc in hexanes) to give 34 mg of the desired product as a colorless oil. MS (ESI) 403 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 30 min
  3. customThe reaction was quenched with 1M aq. NaOH
  4. extractionextracted with EtOAc (3×5 mL)
  5. dry with materialdried over Na2SO4
  6. customThe oil was purified by flash chromatography (silica gel, 0-33% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f4c3cda9387643faac37153d248a7029
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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