Triethylamine → cis-2-Hydroxy-1-{4-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanone

HRID 1809069Notes

Reaction equation

HRID 1809069 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(O)(=O)C.[C:35](Cl)(=[O:38])[CH2:36][OH:37].C[O-].[Na+]>C(Cl)Cl.CO>[OH:38][CH2:35][C:36]([N:21]1[CH2:20][CH2:19][CH:18]([C:16]2[S:15][CH:14]=[C:13]([C:11]([N:1]3[C@@H:10]4[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]4)[CH2:4][CH2:3][CH2:2]3)=[O:12])[CH:17]=2)[CH2:23][CH2:22]1)=[O:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanoneHCID 131730178Glycolic acid chloride acetate

Product 1

HCID 86646704cis-2-Hydroxy-1-{4-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanoneYield 25.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.061 g, 0.18 mmol) in DCM (1 mL) was added triethylamine (0.55 mmol) and glycolic acid chloride acetate (0.24 mmol). The reaction mixture was stirred for 1 hour, and then the solvent evaporated. Methanol (1 mL) and sodium methoxide (0.91 mmol) were added and the reaction mixture was stirred overnight. The solvent was removed by evaporation and the product was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.018 g). LCMS m/z 391.11 [M+H]+ RT=9.24 min (Analytical Method 2).

Workup

  1. customthe solvent evaporated
  2. stirringthe reaction mixture was stirred overnight
  3. customThe solvent was removed by evaporation
  4. customthe product was purified by HPLC
  5. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-bbca1605cde14904990e9517abce5929
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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