HCID 86747727, compound → HCID 6923529, compound

HRID 263479Notes

Reaction equation

HRID 263479 reaction equation
C[C@@H](OC([N:12]1[C@@H:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14](=[O:29])[NH:13]1)=O)C1C=CC=CC=1>[Pd].C1COCC1>[C:23]1([C@H:15]2[C@H:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:12][NH:13][C:14]2=[O:29])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 86747727HCID 86747727, compound

Product 1

HCID 6923529HCID 6923529, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A thick-walled glass hydrogenation tube was charged with diastereomer B of 1-[((R)-α-methylbenzyl)oxycarbonyl]-trans-4,5-diphenyl-3-pyrazolidinone [from Example 139A/139B] (226 mg, 0.586 mmol), 15.0 mL THF and 5% Pd/C catalyst (112 mg) and was shaken on a Parr apparatus under an atmosphere of hydrogen at c. 50 psi pressure for 15.5 hr. The catalyst was filtered off using Celite and washed with THF. The tiltrate was evaporated in vacuo to obtain 134 mg (96%) of a white foam: 1H NMR (CDCl3) δ 3.99 (d, J=l 1 Hz, 1H), 4.66 (br s, 1H), 4.74 (d, J=11 Hz, 1H), 7.20-7.39 (m, 1 OH), 8.63 (br s, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with THF
  3. customThe tiltrate was evaporated in vacuo

Sources & evidence

ORD record
ord-dd1e59345a044bf581ed8129eb039318
Source dataset
uspto-grants-1997_07
Patent number
US05643926

Reaction notes

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