3,3-difluoro-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diaza-spiro[3.5]nonane-1-carboxylic acid benzyl ester → 4-(3,3-difluoro-1,6-diaza-spiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1912422Notes

Reaction equation

HRID 1912422 reaction equation
C(OC([N:11]1[C:14]2([CH2:19][CH2:18][CH2:17][N:16]([C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:15]2)[C:13]([F:30])([F:29])[CH2:12]1)=O)C1C=CC=CC=1>CO.O1CCCC1.[C].[Pd]>[F:30][C:13]1([F:29])[C:14]2([CH2:19][CH2:18][CH2:17][N:16]([C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:15]2)[NH:11][CH2:12]1

Participants

4

Reactant 1

HCID 582932923,3-difluoro-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diaza-spiro[3.5]nonane-1-carboxylic acid benzyl ester

Product 1

HCID 582934094-(3,3-difluoro-1,6-diaza-spiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 81.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of an optically-active compound of 3,3-difluoro-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diaza-spiro[3.5]nonane-1-carboxylic acid benzyl ester (12.0 g) in methanol/tetrahydrofuran (120 ml/120 ml) was added 10% palladium carbon (2.4 g), and the mixture was hydrogenated at room temperature under 4 atmospheres for 21 hours. The mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was slurry-purified by a mixed solvent of n-hexane/ethyl acetate (2/1) to give the titled compound (6.6 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was slurry-purified by a mixed solvent of n-hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-572c7d47255d46b0b23267fa7ded2cac
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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