(3S)-1-Cbz-3-[cyclohexyl(acetyloxypivaloyl)amino]pyrrolidine → (3S)-3-[cyclohexyl(acetyloxypivaloyl)amino]pyrrolidine

HRID 1670009Notes

Reaction equation

HRID 1670009 reaction equation
C([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:17](=[O:26])[C:18]([CH3:25])([CH3:24])[CH2:19][O:20][C:21](=[O:23])[CH3:22])[CH2:12]1)(OCC1C=CC=CC=1)=O>O1CCOCC1.[Pd]>[CH:27]1([N:16]([C:17](=[O:26])[C:18]([CH3:25])([CH3:24])[CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:13]2[CH2:14][CH2:15][NH:11][CH2:12]2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 1

HCID 67345539(3S)-1-Cbz-3-[cyclohexyl(acetyloxypivaloyl)amino]pyrrolidine

Product 1

HCID 67343099(3S)-3-[cyclohexyl(acetyloxypivaloyl)amino]pyrrolidineYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (3S)-1-Cbz-3-[cyclohexyl (acetyloxypivaloyl)amino]pyrrolidine (1.00 g, 2.25 mmol), prepared in Step B, in dioxane (10 mL) was added portionwise Pd/C (200 mg), and the mixture was stirred for 12 h under hydrogen. The reaction solution was filtered though Celite and the filtratae concentrated to give the title compound (657 mg, 84%).

Workup

  1. filtrationThe reaction solution was filtered though Celite
  2. concentrationthe filtratae concentrated

Sources & evidence

ORD record
ord-84864d1d48e64c3887e160a45429e41c
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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