(7s,8r)-Ethyl 8-((r)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt → (7S,8R)-ethyl 8-amino-1,4-dioxaspiro[4.5]decane-7-carboxylate 4-methylbenzenesulfonate

HRID 42536Notes

Reaction equation

HRID 42536 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1([C@H]([NH:20][C@@H:21]2[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][C@@H:22]2[C:31]([O:33][CH2:34][CH3:35])=[O:32])C)C=CC=CC=1>C(O)C.[Pd]>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[NH2:20][C@@H:21]1[CH2:30][CH2:29][C:24]2([O:28][CH2:27][CH2:26][O:25]2)[CH2:23][C@@H:22]1[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

4

Reactant 1

HCID 86645064(7s,8r)-Ethyl 8-((r)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt

Product 1

HCID 86645063(7S,8R)-ethyl 8-amino-1,4-dioxaspiro[4.5]decane-7-carboxylate 4-methylbenzenesulfonateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Pd/C (Degussa, 50% wet, 1.0 g, 9.40 mmol) was carefully wetted down under argon with ethanol, and then (7S,8R)-ethyl 8-((R)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt (10.3 g, 20.37 mmol) in ethanol (75 mL) was added. The mixture was then hydrogenated on a Parr Shaker apparatus for about 16 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give (7S,8R)-ethyl 8-amino-1,4-dioxaspiro[4.5]decane-7-carboxylate p-toluenesulfonic acid salt (8.10 g, 20.18 mmol, 99% yield) as a tacky white glass. MS (ESI+)=230.12 (M+H)+.

Workup

  1. filtrationUnder argon, the reaction was carefully filtered through a fiberglass
  2. filtrationfilter paper
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7efd85ae0eed432e9bc73049f477bd8d
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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