Aluminum isopropoxide → HCID 67996446, compound

HRID 1615170Notes

Reaction equation

HRID 1615170 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@@H:14]([N:16]3[CH2:21][CH2:20][C:19]4([CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]4)[O:18][C:17]3=[O:28])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][C:3]1=[O:29].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Al+3]>C(O)(C)C>[OH:27][CH:24]1[CH2:23][CH2:22][C:19]2([O:18][C:17](=[O:28])[N:16]([C@H:14]([C:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:29])[CH:4]=4)=[CH:9][CH:10]=3)[CH3:15])[CH2:21][CH2:20]2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 67995838HCID 67995838, compound

Product 1

HCID 67996446HCID 67996446, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-{(S)-1-[4-(1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-phenyl]-ethyl}-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione (130 mg), aluminum triisopropoxide (100 mg), and isopropanol (2 mL) is stirred at 140° C. for 1 h. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to afford the title compound in a ca. 1:1 mixture of cis- and trans-isomer. Yield: 72% of theory; LC (method 2): tR=1.49 and 1.51 min; Mass spectrum (ESI+): m/z=397 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by HPLC on reversed phase (methanol/water)

Sources & evidence

ORD record
ord-3df34ba1cf9347ebbd80101d784b55ea
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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