Tetrabutylammonium Fluoride → HCID 68537529, compound

HRID 655538Notes

Reaction equation

HRID 655538 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C@H:32]([C:41](C2C=CC=CC=2)(C2C=CC=CC=2)[O:42][SiH2]C(C)(C)C)[CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:28](=[O:60])[C@@H:27]1[CH3:61])=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C@H:32]([CH2:41][OH:42])[CH2:33][CH2:34][N:35]2[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)[C:28](=[O:60])[C@@H:27]1[CH3:61])=[O:25])([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 131729301HCID 131729301, compound

Product 1

HCID 68537529HCID 68537529, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride solution (1 M in tetrahydrofuran, 0.14 mL, 0.14 mmol) was added at room temperature to a solution of (S)-4-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-piperidin-1-yl-propyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (75 mg, 0.12 mmol) in tetrahydrofuran (1 mL), then after 16 h another portion of tetrabutylammonium fluoride solution (1 M in tetrahydrofuran, 20 μL, 20 μmol) was added. The reaction mixture was stirred at room temperature for another 60 min, then evaporated. Chromatography (SiO2; dichloromethane dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) produced the title compound (42 mg, 92%). Colorless gum, MS (ISP)=370.3 (M+H)+.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-f9b5e0d8b07d47bd879f005c9c44eba8
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

Loading…