Potassium Carbonate → HCID 86609732, compound

HRID 2389950Notes

Reaction equation

HRID 2389950 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[C:19]3[C:14]([C@H:15]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[C:31][Si](C)(C)C)[CH:25]=4)[CH2:16][N:17]4[CH2:23][CH2:22][CH2:21][C@H:18]43)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+]>CO>[C:30]([C:26]1[CH:25]=[C:24]([C@H:15]2[C:14]3[C:19](=[CH:20][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:12][CH:13]=3)[C@@H:18]3[CH2:21][CH2:22][CH2:23][N:17]3[CH2:16]2)[CH:29]=[CH:28][CH:27]=1)#[CH:31]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67542636HCID 67542636, compound

Product 1

HCID 86609732HCID 86609732, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cis-9-(3-piperidin-1-yl-propoxy)-6-(3-trimethylsilanylethynyl-phenyl)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline (Example 33, 40.0 mg, 0.082 mmol) and K2CO3 (2.0 mg, 0.008 mmol) in MeOH (4.1 mL, 0.2 M) was stirred for 2 h at rt. The crude reaction mixture was purified directly after filtration by reverse-phase HPLC to give 19.0 mg (36%) of the desired product as a TFA salt. MS: exact mass calcd for C28H34N2O, 414.3; m/z found, 415.5 [M+H]+. 1H NMR (acetone-d6): 7.45 (m, 4H), 6.96 (m, 1H), 6.79 (dd, J=3.2, 10.9, 1H), 6.64 (d, J=10.9, 1H), 4.92 (m, 1H), 4.62 (m, 1H), 4.12 (t, J=7.5, 2H), 3.93 (m, 1H), 3.66 (m, 4H), 3.51 (m, 1H), 3.39 (m, 1H), 3.31 (m, 2H), 2.93 (m, 3H), 2.32 (m, 5H), 1.89 (m, 5H), 1.51 (m, 1H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly
  3. filtrationafter filtration by reverse-phase HPLC

Sources & evidence

ORD record
ord-de1779608edc4e9797d7b74f6ce657a4
Source dataset
uspto-grants-2012_09
Patent number
US08273762B2

Reaction notes

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