5-(p-Fluorophenyl)-2-hydroxytetrahydrofuran → Flutroline

HRID 255690Notes

Reaction equation

HRID 255690 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]3[CH2:18][CH2:19][N:20]([C:22](OCC4C=CC=CC=4)=O)[CH2:21][C:5]=3[C:4]=2[CH:3]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[O:43]C(O)[CH2:41][CH2:40]2)=[CH:35][CH:34]=1>C(OCC)(=O)C.[Pd]>[F:17][C:14]1[CH:15]=[CH:16][C:11]2[N:7]([C:8]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[C:6]3[CH2:5][CH2:21][N:20]([CH2:22][CH2:41][CH2:40][CH:39]([C:36]4[CH:35]=[CH:34][C:33]([F:32])=[CH:38][CH:37]=4)[OH:43])[CH2:19][C:18]=3[C:12]=2[CH:13]=1

Participants

5

Reactant 2

HCID 118300545-(p-Fluorophenyl)-2-hydroxytetrahydrofuranHCID 13374324HCID 13374324, compound

Product 1

HCID 51174Flutroline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

In a Parr bottle were combined 5% Pd/C (5 g of 50% water-wet), 8-fluoro-5-(p-fluorophenyl)-2-carbobenzoxy-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (5.0 g, 0.0119 mole) in 100 ml ethyl acetate, and 5.5 grams (0.03 mole) 5-(p-fluorophenyl)-2-hydroxytetrahydrofuran in 100 ml ethyl acetate. The mixture was agitated and hydrogenated at 30-40 psig for 20 hours. The solution was filtered to recover catalyst, with ethyl acetate and CH2Cl2 wash. The filtrate and washes were concentrated in vacuo to a viscous oil. The oil was dissolved in 400 ml ethyl acetate and filtered. The solution was concentrated to an oil, diluted with 150 ml ether, and filtered to yield title product, 3.8 gm, m.p. 145°-149° C.

Workup

  1. filtrationThe solution was filtered
  2. customto recover catalyst
  3. washwith ethyl acetate and CH2Cl2 wash
  4. concentrationThe filtrate and washes were concentrated in vacuo to a viscous oil
  5. dissolutionThe oil was dissolved in 400 ml ethyl acetate
  6. filtrationfiltered
  7. concentrationThe solution was concentrated to an oil
  8. additiondiluted with 150 ml ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8c03bff6118d4f1faa67a5d32fd87da9
Source dataset
uspto-grants-1987_10
Patent number
US04698444

Reaction notes

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