Acetic Acid → HCID 59813165, compound

HRID 2115197Notes

Reaction equation

HRID 2115197 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)=[C:10]2[CH2:16][CH:15]3[NH:17][CH:12]([CH2:13][CH2:14]3)[CH2:11]2)[CH:6]=[CH:7][CH:8]=1.[CH3:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(OC)(OC)OC.C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)=[C:10]2[CH2:11][CH:12]3[N:17]([CH2:23][C:24]4[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=4[CH3:26])[CH:15]([CH2:14][CH2:13]3)[CH2:16]2)[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 107222-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11266931HCID 11266931, compound

Product 1

HCID 59813165HCID 59813165, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

To 100 mg (321 μmol) of 3-[(3-Methoxy-phenyl)-thiophen-3-yl-methylene]-8-aza-bicyclo[3.2.1]octane in 1 mL of trimethyl orthoformate was added 56 μL (482 μmol) of 2-methylbenzaldehyde, 156 mg (739 μmol) of sodium triacetoxyborohydride, 34 μL of glacial acetic acid at room temperature. The reaction mixture was allowed to stir 10 days at room temperature. After 10 days, the crude was diluted with 1 mL of DCM and 0.5 mL of MeOH. The diluted solution was filtered and washed with 1 mL of DCM. The combined filtrates were concentrated. The concentrated sample was purified using Biotage NH2-silica column using a gradient of 5% ethyl acetate/hexane to 40% ethyl acetate/hexane. The eluent was evaporated to yield 133 mg of the title compound as a white solid; MS m/z (MH+) 416.

Workup

  1. waitAfter 10 days
  2. filtrationThe diluted solution was filtered
  3. washwashed with 1 mL of DCM
  4. concentrationThe combined filtrates were concentrated
  5. customThe concentrated sample was purified
  6. customThe eluent was evaporated

Sources & evidence

ORD record
ord-7b808cd5340d4b02a681cd69ec81fcf5
Source dataset
uspto-grants-2008_10
Patent number
US07435822B2

Reaction notes

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