Oxygen → (2S,4S)-1-[(benzyloxy)carbonyl]-4-cyclohexylpyrrolidine-2-carboxylic acid

HRID 280379Notes

Reaction equation

HRID 280379 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][C@H:12]1[CH2:22][OH:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:25].[Na+].O1CCOCC1.O=O>[Pt].O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:13][C@H:12]1[C:22]([OH:25])=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 13648262(2S-trans)-1-[(Benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol

Product 1

HCID 54164240(2S,4S)-1-[(benzyloxy)carbonyl]-4-cyclohexylpyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

To a mixture of (2S-trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol (0.65 g), sodium bicarbonate (0.5 g), dioxane (20 ml), and water (20 ml) was added freshly prepared platinum black (prepared by hydrogenating 0.3 g of platinum oxide). Oxygen was passed through the solution at room temperature for 16 hours with vigorous stirring. Filtration and acidification, followed by extractive work-up yielded (trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-L-proline as a glassy solid. This compound can be deprotected using catalytic hydrogenation as described in Method I.

Workup

  1. filtrationFiltration and acidification

Sources & evidence

ORD record
ord-10f12a3bfc104217b43b560179c543b0
Source dataset
uspto-grants-1986_05
Patent number
US04588819

Reaction notes

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