Triethylamine → 4-(2-Hydroxy-ethoxy)-phenyl-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 552582

Reaction equation

HRID 552582 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCl>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:11])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 2724699PyBOPHCID 43122544-(2-Hydroxyethoxy)benzenecarboxylic acid

Product 1

HCID 119604194-(2-Hydroxy-ethoxy)-phenyl-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanoneYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(2-Hydroxy-ethoxy)-benzoic acid (152 mg, 0.84 mmol), (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (193 mg, 1.25 mmol) and triethylamine (303 mg, 3.0 mmol) are dissolved in dichloromethane (5.0 mL) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP) (786 mg, 1.5 mmol) is added to the mixture. The mixture is stirred at room temperature for 3 days. The reaction mixture is diluted with dichloromethane, washed with brine, dried over Na2SO4, filtered and evaporated. The crude product is purified using silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=20:1) to give 177 mg (66%) of the title compound. Observed Mass 319.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified

Sources & evidence

ORD record
ord-6607de3a9eb3496199ab018dd70bd4ee
Source dataset
uspto-grants-2011_05
Patent number
US07951826B2

Linked notes

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