HCID 90079870, compound → HCID 90080019, compound

HRID 1771963Notes

Reaction equation

HRID 1771963 reaction equation
[CH:1]1([CH2:4][C@H:5]([C@H:16]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6]([O:8]CC2C=CC=CC=2)=[O:7])[CH2:3][CH2:2]1>CO.[Pd]>[C:20]([O:19][C:17](=[O:18])[C@@H:16]([CH2:24][CH:25]1[CH2:26][CH2:27]1)[C@@H:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[C:6]([OH:8])=[O:7])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 90079870HCID 90079870, compound

Product 1

HCID 90080019HCID 90080019, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,3S)-1-benzyl 4-tert-butyl 2,3-bis(cyclopropylmethyl)succinate, Intermediate S8G (0.530 g, 1.423 mmol) in MeOH (10 mL) was added 10% Pd/C (Degussa) (0.300 g, 1.423 mmol). The reaction mixture was evacuated with vacuum and filled with H2 (Repeated this for 3×). Next, the reaction mixture was stirred under H2 balloon for 1.5 h, evacuated, and filled with N2. The mixture was then filtered through CELITE®. The filtrate was concentrated to afford (2R,3S)-4-(tert-butoxy)-2,3-bis(cyclopropylmethyl)-4-oxobutanoic acid, Intermediate S8 (0.400 g, 1.417 mmol, 100% yield) as a colorless liquid. 1H NMR (400 MHz, chloroform-d) δ 2.69 (td, J=9.9, 3.7 Hz, 2H), 1.71-1.54 (m, 2H), 1.47 (s, 9H), 1.38-1.22 (m, 2H), 0.80-0.62 (m, 2H), 0.51-0.36 (m, 4H), 0.16-0.05 (m, 2H), 0.05-−0.02 (m, 2H).

Workup

  1. customThe reaction mixture was evacuated with vacuum
  2. additionfilled with H2 (
  3. customevacuated
  4. additionfilled with N2
  5. filtrationThe mixture was then filtered through CELITE®
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-00dce0db0cf24b7d912edfaa5c2c3567
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

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