Water → HCID 25073714, compound

HRID 1944193Notes

Reaction equation

HRID 1944193 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:29][CH3:30])=[C:13]([O:18][Si](C(C)C)(C(C)C)C(C)C)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][CH2:32][CH2:33]C[N+](CCCC)(CCCC)CCCC.[F-].C1C[O:52]CC1.O>C1COCC1>[CH:32]([O:52][C:6]1[CH:7]=[C:2]([CH:3]=[CH:4][CH:5]=1)[CH2:1][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:29][CH3:30])=[C:13]([OH:18])[CH:14]=2)[CH2:9]1)([CH3:33])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 68497020HCID 68497020, compound

Product 1

HCID 25073714HCID 25073714, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-benzyl-7-methoxy-6-triisopropylsilyloxy-1,2,3,4-tetrahydroisoquinoline (1 mmol) in THF (20 mL) was stirred with a 1M solution of TBAF/THF (1.1 mmol) for 60 minutes at RT. After addition of water, the organics were extracted with ethyl acetate (80 mL) and the organic layer washed with water, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residual oil/solid was purified by flash chromatography (hexane/ethyl acetate).

Workup

  1. extractionthe organics were extracted with ethyl acetate (80 mL)
  2. washthe organic layer washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residual oil/solid was purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-45448537dd7740b2a09e476728179c1d
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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