Sodium Bicarbonate → HCID 21993917, compound

HRID 1978322Notes

Reaction equation

HRID 1978322 reaction equation
[O:1]([CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][N:24]([CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:23]2)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:32]1([CH2:31][CH2:30][CH2:29][N:24]2[CH2:23][C:22]3[C:26](=[CH:27][CH:28]=[C:20]([CH2:19][OH:1])[CH:21]=3)[CH2:25]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11078149TBAF tetrahydrofuranHCID 21993759HCID 21993759, compound

Product 1

HCID 21993917HCID 21993917, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.699 g (7.316 mM) of 5-(tert-butyldiphenylsiloxymethyl)-2-(3-phenylpropan-1-yl)-2,3-dihydro-1H-isoindole in 50 ml of tetrahydrofuran was added 8.78 ml (8.78 mM) of 1.0N-tetrabutylammonium fluoride-tetrahydrofuran at room temperature and the mixture was stirred for 1 hour. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate) to provide the title compound.

Workup

  1. extractionextracted with 3 portions of ethyl acetate
  2. dry with materialThe pooled organic layer was dried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-7ecb596d93424252899b5d08402511ef
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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