HCID 58293293, compound → Tert-butyl 3,3-difluoro-1,6-diazaspiro[3.4]octane-6-carboxylate

HRID 1912412Notes

Reaction equation

HRID 1912412 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][C:10]2([N:13](C(OCC3C=CC=CC=3)=O)[CH2:12][C:11]2([F:25])[F:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][C:10]2([NH:13][CH2:12][C:11]2([F:24])[F:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58293293HCID 58293293, compound

Product 1

HCID 58293289Tert-butyl 3,3-difluoro-1,6-diazaspiro[3.4]octane-6-carboxylateYield 81.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of an optically-active compound of 3,3-difluoro-1,6-diazaspiro[3,4]octane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester (397 mg) in methanol/tetrahydrofuran (3.2 ml/3.2 ml) was added 10% palladium carbon (79 mg), and the mixture was hydrogenated at room temperature under ordinary pressure for 14 hours. The mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=4/1 to 2/1). The fractions which could not be separated and isolated were concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=2/1 to 1/1) again. The purified fractions were combined and concentrated under reduced pressure to give the titled compound (211 mg).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=4/1 to 2/1)
  4. customThe fractions which could not be separated
  5. customisolated
  6. concentrationwere concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform/acetone=2/1 to 1/1) again
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2be502d5a74482d8c3148741bf3884d
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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