Water → HCID 69033957, compound

HRID 2086902Notes

Reaction equation

HRID 2086902 reaction equation
[CH2:1]([C:5]1(O)[CH2:30][N:9]2[C@H:10]([C:26](C)(C)C)[CH2:11][C:12]3[C:17]([CH:8]2[CH:7](CO[SiH3])[C:6]1=[O:34])=[C:16](OC)[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[C:13]=3OC)[CH2:2][CH2:3][CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH2:54]>C1COCC1>[CH2:1]([CH:5]1[CH2:30][N:9]2[C@H:10]([CH2:26][OH:54])[CH2:11][C:12]3[C:17]([CH:8]2[CH2:7][C:6]1=[O:34])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131724421HCID 131724421, compound

Product 1

HCID 69033957HCID 69033957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.40 g of (6S)-3-Butyl-3-hydroxy-6-tert-butyldimethoxy-siloxymethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one in 13 ml of THF at 0° C. was slowly added a solution of 1.78 ml of tetrabutylammonium fluoride (1M in THF). The reaction mixture was stirred for 2 hours keeping the temperature between 0-5° C. The reaction mixture was poured into ice cooled water (49 ml) and then extracted two times with 30 ml of ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was then purified by chromatography (silica gel, hexane/ethyl acetate 0-70%) to give 0.30 g of (6S)-3-Butyl-6-hydroxymethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one, MS (ISP) 348.3 (M+H)+.

Workup

  1. custombetween 0-5° C
  2. additionThe reaction mixture was poured into ice
  3. extractionextracted two times with 30 ml of ethyl acetate
  4. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by chromatography (silica gel, hexane/ethyl acetate 0-70%)

Sources & evidence

ORD record
ord-6f5413ba9d3a4018993c851f462989ff
Source dataset
uspto-grants-2004_04
Patent number
US06727261B2

Reaction notes

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