9-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester → 9-hydroxy-9-fluorenylcarbonyl-L-proline

HRID 1058306Notes

Reaction equation

HRID 1058306 reaction equation
C([O:8][C:9](=[O:31])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([C:17]1([OH:30])[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:30][C:17]1([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([OH:31])=[O:8])=[O:16])[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2

Participants

4

Reactant 1

HCID 590381919-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester

Product 1

HCID 590382169-hydroxy-9-fluorenylcarbonyl-L-proline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-hydroxy-9-fluorenylcarbonyl-L-proline benzyl ester (3.8 g, 9.3 mmol) from step 1 above and 10% palladium on carbon (390 mg) in ethyl acetate (100 mL) was stirred under an atmosphere of hydrogen (balloon pressure) for 24 hours. The mixture was filtered through celite and concentrated in vacuo to give 9-hydroxy-9-fluorenylcarbonyl-L-proline. HPLC=90%, R.T.=2.97 min, method A; M+1=324.1; 1H NMR (CD3OD) 7.78-7.75 (m, 2H), 7.47-7.32 (m, 6H), 4.49-4.45 (q, 1H), 2.42-2.30 (m, 2H), 2.01-1.94 (m, 1H), 1.78-1.71 (m, 1H), 1.58-1.41 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-797e3815b10e49ccbb902ce4ded5020a
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

Loading…