Proton sponge → HCID 68690847, compound

HRID 1159050Notes

Reaction equation

HRID 1159050 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][N:11]2[C:12](=[O:25])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][C:14]=3[C:21]([F:24])([F:23])[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28]N(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][N:11]2[C:12](=[O:25])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][O:20][CH3:28])=[CH:15][C:14]=3[C:21]([F:22])([F:24])[F:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 68688454HCID 68688454, compound

Product 1

HCID 68690847HCID 68690847, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-hydroxymethyl-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (30 mg, 0.08 mmol) and proton sponge (26 mg, 0.12 mmol) in dry CH2Cl2 (1.0 mL) was added trimethyloxonium tetrafluoroborate (11.5 mg, 0.08 mmol). The reaction was stir for 16 hr and then quenched with 1M aq. HCl. The reaction was extracted with EtOAc (3×10 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pink oil. The oil was purified by flash chromatography (silica gel, 0-40% EtOAc in hexanes) to yield 13 mg of the desired product as a colorless oil. MS (ESI) 401 (M+H).

Workup

  1. customquenched with 1M aq. HCl
  2. extractionThe reaction was extracted with EtOAc (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. customThe oil was purified by flash chromatography (silica gel, 0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b935e01ff7ea431e8d88e060134fc38f
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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