Water → HCID 67249245, compound

HRID 2175090Notes

Reaction equation

HRID 2175090 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:31]=[CH:30][C:29]4[C:28]([CH3:33])([CH3:32])[CH2:27][CH2:26][C:25]([CH3:35])([CH3:34])[C:24]=4[CH:23]=3)[N:17]=2)[CH2:12][CH2:11]1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.O.C(OCC)(=O)C>C1COCC1>[CH3:32][C:28]1([CH3:33])[CH2:27][CH2:26][C:25]([CH3:34])([CH3:35])[C:24]2[CH:23]=[C:22]([C:18]3[N:17]=[C:16]([N:13]4[CH2:12][CH2:11][N:10]([CH2:9][CH:7]5[CH2:8][CH:6]5[CH2:4][OH:3])[CH2:15][CH2:14]4)[CH:21]=[CH:20][CH:19]=3)[CH:31]=[CH:30][C:29]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 67248465HCID 67248465, compound

Product 1

HCID 67249245HCID 67249245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg (0.21 mmol) of 2-{4-[6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridin-2-yl]piperazin-1-ylmethyl}cyclopropanecarboxylic acid ethyl ester is dissolved in 4 ml of THF, and 1.05 ml (1.05 mmol) of diisobutylaluminium hydride (1.0 M in THF) are added. The reaction mixture is stirred at room temperature under nitrogen atmosphere for 18 h. Water is added to the reaction mixture, which is then briefly stirred, ethyl acetate is added, and the mixture is filtered through Celite. The filter cake is washed with ethyl acetate and methanol, and the mother liquor is evaporated. The residue is purified by column chromatography on silica gel.

Workup

  1. stirringis then briefly stirred
  2. filtrationthe mixture is filtered through Celite
  3. washThe filter cake is washed with ethyl acetate and methanol
  4. customthe mother liquor is evaporated
  5. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-124f4b9a0a854454a1ffbec056b84a93
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

Loading…