Tetrahydrofuran → HCID 9815102, compound

HRID 983905Notes

Reaction equation

HRID 983905 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([CH2:12][CH2:13][CH2:14]3)=[C:10]([C:16](OCC)=[O:17])[C:9]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.C1COCC1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([CH2:12][CH2:13][CH2:14]3)=[C:10]([CH2:16][OH:17])[C:9]=2[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 9946393Ethyl 3-(4-fluorophenyl)-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolizine-1-carboxylate

Product 1

HCID 9815102HCID 9815102, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-(4-fluorophenyl)-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolizine-1-carboxylate (example 1A, 4.56 g, 13 mmol) is dissolved in abs. THF (100 ml) under argon and Na bismethoxyethoxyaluminum hydride (VitrideR) is added dropwise through a septum via the cannula of a syringe (20 min). The mixture is stirred at 50° C. for 2 h, whereupon starting material is no longer detectable by tlc (Al2O3—ethyl acetate/n-hexane 3:7), then it is allowed to cool. H2O (25 ml) is cautiously added dropwise to the reaction solution, then it is concentrated in vacuo (THF evaporates), and the aqueous organic residue is treated with ethyl acetate (100 ml). The phases are separated. The organic phase is washed 2 times with water (40 ml), dried over Na2SO4 sicc. and concentrated in vacuo (5.0 g). The reddish brown-colored, resinous residue is crystallized from diethyl ether (10 ml). The crystals are washed with ethyl acetate (5 ml) and ether (5 ml) and dried. 3.67 g of the compound sought remain

Workup

  1. temperatureto cool
  2. concentrationit is concentrated in vacuo (THF evaporates)
  3. additionthe aqueous organic residue is treated with ethyl acetate (100 ml)
  4. customThe phases are separated
  5. washThe organic phase is washed 2 times with water (40 ml)
  6. dry with materialdried over Na2SO4 sicc
  7. concentrationand concentrated in vacuo (5.0 g)
  8. customThe reddish brown-colored, resinous residue is crystallized from diethyl ether (10 ml)
  9. washThe crystals are washed with ethyl acetate (5 ml) and ether (5 ml)
  10. customdried

Sources & evidence

ORD record
ord-463266a2f6f7453f950fe76e1a1be0ba
Source dataset
uspto-grants-2005_03
Patent number
US06867211B2

Reaction notes

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