(1R,3S,5R)-2-[2-(3-Acetyl-pyrazolo[3,4-c]pyridin-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester → (1R,3S,5R)-2-[2-(3-Acetyl-pyrazolo[3,4-c]pyridin-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid

HRID 1052128Notes

Reaction equation

HRID 1052128 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:16][C@@H:15]2[C@@H:13]([CH2:14]2)[N:12]1[C:17](=[O:31])[CH2:18][N:19]1[C:23]2=[CH:24][N:25]=[CH:26][CH:27]=[C:22]2[C:21]([C:28](=[O:30])[CH3:29])=[N:20]1)=[O:10])C1C=CC=CC=1>C1COCC1.[Pd]>[C:28]([C:21]1[C:22]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[N:19]([CH2:18][C:17]([N:12]2[C@H:11]([C:9]([OH:10])=[O:8])[CH2:16][C@@H:15]3[C@H:13]2[CH2:14]3)=[O:31])[N:20]=1)(=[O:30])[CH3:29]

Participants

4

Reactant 1

HCID 90019996(1R,3S,5R)-2-[2-(3-Acetyl-pyrazolo[3,4-c]pyridin-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Product 1

HCID 71009551(1R,3S,5R)-2-[2-(3-Acetyl-pyrazolo[3,4-c]pyridin-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,3S,5R)-2-[2-(3-acetyl-pyrazolo[3,4-c]pyridin-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (2.26 g, 5.4 mmol) in THF (20 mL) was added Pd/C 10% (60 mg). The reaction was placed under hydrogen atmosphere and was stirred for 72 h. The catalyst was removed by filtration through a pad of Celite and washed with MeOH. Solvents were concentrated to give the title compound. MS (UPLC-MS): 329 [M+H]+; tR (HPLC conditions d): 2.29 min.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. washwashed with MeOH
  3. concentrationSolvents were concentrated

Sources & evidence

ORD record
ord-426dbfc67bf1485690957ec05eb3c5e9
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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