Acetic Acid → HCID 58997721, compound

HRID 42534Notes

Reaction equation

HRID 42534 reaction equation
C(O)(=O)C.[C:5]1([C@H:11]([NH:13][C:14]2[CH2:23][CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][C:15]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.CCOC(C)=O.[Pt]>[C:5]1([C@H:11]([NH:13][C@@H:14]2[CH2:23][CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][C@@H:15]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 58997675HCID 58997675, compound

Product 1

HCID 58997721HCID 58997721, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5% Pt/C (Sigma-Aldrich catalog #205931, 0.80 g, 30.2 mmol) was carefully wetted down under argon with ethanol. Acetic acid (5.30 mL, 93 mmol) was added thereto followed by (R)-ethyl 8-(1-phenylethylamino)-1,4-dioxaspiro[4.5]dec-7-ene-7-carboxylate (prepared in a similar manner as that described in International Patent Application No. WO 2005/048932, 10.0 g, 30.2 mmol) in ethanol (50 mL). The reaction was then hydrogenated at 50 psi for about 16 hours with stirring in a Parr Shaker apparatus. The catalyst was carefully filtered under argon and the filtrate concentrated to yield an amber oil. The oil was dissolved in EtOAc then rinsed with 5% Na2HPO4 until pH=8-9 (5 rinses). The EtOAc layer was dried over sodium sulfate and concentrated to give (7S,8R)-ethyl 8-((R)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate (5.40 g, 16.2 mmol, 54% yield) as an amber oil. MS (ESI+)=334.25 (M+H)+.

Workup

  1. customprepared in a similar manner as
  2. filtrationThe catalyst was carefully filtered under argon
  3. concentrationthe filtrate concentrated
  4. customto yield an amber oil
  5. washthen rinsed with 5% Na2HPO4 until pH=8-9 (5 rinses)
  6. dry with materialThe EtOAc layer was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2f2b1b24472f45f2a016c133665718d5
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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