Ethanol → HCID 178498787, compound

HRID 713960Notes

Reaction equation

HRID 713960 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([C:22](=O)[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][O:26][C:27]([CH:29]1[CH2:32][NH:31][CH2:30]1)=[O:28].C(O)C.C([BH3-])#N.[Na+]>>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([CH:22]([N:31]2[CH2:32][CH:29]([C:27]([O:26][CH3:25])=[O:28])[CH2:30]2)[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 20132751Methyl azetidine-3-carboxylateHCID 66926615HCID 66926615, compound

Product 1

HCID 178498787HCID 178498787, compoundYield 65.1%

Procedure

1-[6-(4-tert-Butyl-cyclohexyloxy)-quinolin-2-yl]-ethanone (68 mg, 0.00021 mol) and Azetidine-3-carboxylic acid methyl ester (23.9 mg, 0.000207 mol) was dissolved in Ethanol (0.50 mL, 0.0086 mol) and was heated to reflux for 2 hours. After cooling down to rt, Sodium cyanoborohydride (32.4 mg, 0.000516 mol) was added and was heated to reflux for 1 hour. After cooling down to rt and concentration, the mixture was dissolved into DCM and quenched with NEt3 and concentrated. The residue was chromatographed with MeOH/CH2Cl2 to give product (57.2 mg, 65%). LCMS 1.66 min, at m/z 425.30 ([M+1], 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperaturewas heated
  4. temperatureto reflux for 1 hour
  5. temperatureAfter cooling down to rt
  6. concentrationconcentration
  7. dissolutionthe mixture was dissolved into DCM
  8. customquenched with NEt3
  9. concentrationconcentrated
  10. customThe residue was chromatographed with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-ed8b8d0b51b940aea75e9adc1abcd086
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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