Tetrabutylammonium Fluoride → HCID 57888692, compound

HRID 1016160Notes

Reaction equation

HRID 1016160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:32])[C:13]3([CH2:15][CH2:14]3)[CH2:12][N:11]([C:16](=[O:31])[C@H:17]([NH:21]C(=O)OCC[Si](C)(C)C)[CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:21][C@H:17]([CH:18]([CH3:20])[CH3:19])[C:16]([N:11]1[CH2:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:32])[C:13]2([CH2:15][CH2:14]2)[CH2:12]1)=[O:31]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86614928HCID 86614928, compound

Product 1

HCID 57888692HCID 57888692, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(trimethylsilyl)ethyl (2R)-1-(8-(4-chlorophenyl)-8-hydroxy-5-azaspiro[2.5]octan-5-yl)-3-methyl-1-oxobutan-2-ylcarbamate (754 mg, 1.567 mmol) in THF (10 mL) was treated with TBAF (1.0 M in THF) (6.27 mL, 6.27 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in-vacuo, and the residue was partitioned between EtOAc and saturated sodium bicarbonate. The layers were separated, and the organic phase was washed 2× with saturate sodium bicarbonate, once with water, and once with brine. The combined aqueous phases were extracted once with ethyl acetate, and the combined organic phases were washed with water and brine, then dried over sodium sulfate and concentrated in-vacuo. The residue was taken up in acetonitrile (100 mL), and washed 3× with 20 mL of hexanes. The acetonitrile phase was concentrated in-vacuo to yield the title compound (420 mg, 1.247 mmol, 80% yield) as a colorless glass. MS (ESI+)=337.4, (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in-vacuo
  2. customthe residue was partitioned between EtOAc and saturated sodium bicarbonate
  3. customThe layers were separated
  4. washthe organic phase was washed 2× with saturate sodium bicarbonate
  5. extractionThe combined aqueous phases were extracted once with ethyl acetate
  6. washthe combined organic phases were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in-vacuo
  9. washwashed 3× with 20 mL of hexanes
  10. concentrationThe acetonitrile phase was concentrated in-vacuo

Sources & evidence

ORD record
ord-0ef015a0da0b4858a255e7cf9a768e7f
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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