HCID 21182740, compound → HCID 21182720, compound

HRID 1386993Notes

Reaction equation

HRID 1386993 reaction equation
[S:1]1[C:5]([C:6]2[CH:20]=[CH:19][C:9](/[CH:10]=[CH:11]/[C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=O)=[CH:8][CH:7]=2)=[CH:4][C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[S:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][CH2:11][CH2:12][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)=[CH:19][CH:20]=2)=[CH:4][C:3]2[CH:21]=[CH:22][CH:23]=[CH:24][C:2]1=2

Participants

4

Reactant 2

HCID 21182740HCID 21182740, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21182720HCID 21182720, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.2 g (3.6 mmol) of 1-[trans-4-(benzo[b]thiophen-2-yl)cinnamoyl]pyrrolidine (Part B) in 15 mL of THF was treated with 75 mg (2.0 mmol) of LiAlH4 at −15° C. After complete consumption of starting material, the reaction was cautiously quenched with H2O. The mixture was extracted with EtOAc and the combined organic layers were evaporated in vacuo. Chromatography afforded 600 mg (1.9 mmol; 52% yield) of the desired product.

Workup

  1. customAfter complete consumption of starting material
  2. customthe reaction was cautiously quenched with H2O
  3. extractionThe mixture was extracted with EtOAc
  4. customthe combined organic layers were evaporated in vacuo

Sources & evidence

ORD record
ord-05a6a0afdfa74cdf9c88c769e9e40205
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…