Triethylamine → HCID 53629157, compound

HRID 1926737Notes

Reaction equation

HRID 1926737 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8]CC)=O.[C:17]([N:36]1[CH:40]=[C:39]([CH:41]=O)[N:38]=[CH:37]1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[BH4-].[Na+]>O.C(Cl)Cl.CO>[C:11]1([CH:4]2[CH2:3][N:2]([CH2:41][C:39]3[N:38]=[CH:37][N:36]([C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:40]=3)[C:6](=[O:8])[CH2:5]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 2959448HCID 2959448, compoundHCID 4311764Sodium borohydride

Product 1

HCID 53629157HCID 53629157, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a 500 ml, three-necked flask fitted with a magnetic stirrer and a reflux condenser under inert atmosphere, ethyl 4-amino-3-phenylbutanoate hydrochloride x42 (synthesized as described in patent application EP1265862, 6.2 g, 38 mmol), 1-trityl-1H-imidazole-4-carbaldehyde x43 (Dolensky B., Kirk K. L., Collect. Czech. Chem. Commun. (2002), 67, 1335-1344; 8.2 g, 36.1 mmol) and MeOH (150 ml) are stirred at room temperature. Triethylamine (3.9 ml, 41.85 mmol) and NaBH4 (1.06 g, 41.8 mmol) are added by portions. The mixture is stirred at 45° C. for 3 h, then at room temperature overnight. CH2Cl2 (300 ml) and water (300 ml) are added, the aqueous phase is extracted with CH2Cl2 (2×200 ml). The combined organic phases are washed with a saturated solution of NH4Cl (2×150 ml), dried, filtered and concentrated in vacuo. The crude product is recrystallized from AcOEt to afford 4-phenyl-1-[(1-trityl-1H-imidazol-4-yl)methyl]pyrrolidin-2-one x44.

Workup

  1. stirringThe mixture is stirred at 45° C. for 3 h
  2. customat room temperature
  3. customovernight
  4. extractionthe aqueous phase is extracted with CH2Cl2 (2×200 ml)
  5. washThe combined organic phases are washed with a saturated solution of NH4Cl (2×150 ml)
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product is recrystallized from AcOEt

Sources & evidence

ORD record
ord-f97fa4de392641579371c9ad4898814f
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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