Acetic Acid → HCID 68510097, compound

HRID 1714027Notes

Reaction equation

HRID 1714027 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23])[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH:32]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38].C(O)(=O)C.[BH4-].[Na+]>C1COCC1>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23])[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][NH:38][CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 4311764Sodium borohydrideHCID 86604965HCID 86604965, compound

Product 1

HCID 68510097HCID 68510097, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of methyl 3-cyclohexyl-1-(2,2-dimethoxyethyl)-2-(2-formylphenyl)-1H-indole-6-carboxylate (0.16 M, 1 eq, from Step 2) and 2-dimethylaminoethylamine (2 eq) in THF was added glacial acetic acid to adjust the pH of the reaction to ca. pH 4. The reaction was stirred for 1 h after which the THF was removed under reduced pressure and the residue redissolved in MeOH. NaBH4 (8 eq) was added portionwise until complete conversion was observed by LC-MS analysis. The reaction was quenched by addition of sat. aq. NaHCO3 and extracted into EtOAc (×3). The combined organics were washed with H2O and brine before being dried (Na2SO4), filtered and concentrated in vacuo. The title compound was obtained as a pale yellow oil and taken on without further purification (quantitative); MS (ES+) m/z 522 (M+H)+.

Workup

  1. customthe pH of the reaction to ca. pH 4
  2. customwas removed under reduced pressure
  3. dissolutionthe residue redissolved in MeOH
  4. customThe reaction was quenched by addition of sat. aq. NaHCO3
  5. extractionextracted into EtOAc (×3)
  6. washThe combined organics were washed with H2O and brine
  7. dry with materialbefore being dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de1bbe2741c14ae3bb32de64a36739f9
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

Loading…