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

HRID 857729Notes

Reaction equation

HRID 857729 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; M+1=324.1; 1H NMR (CD3OD, 400 MHz) δ 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-2da3ee06c64b44858abef4950f4d57b8
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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