HCID 58293367, compound → 3-Methyl-1,6-diazaspiro[3.4]octane-1-carboxylic acid tert-butyl ester

HRID 1912433Notes

Reaction equation

HRID 1912433 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:11]2([CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12]2)[CH:10]([CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.CO.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[C:1]([O:5][C:6]([N:8]1[C:11]2([CH2:15][CH2:14][NH:13][CH2:12]2)[CH:10]([CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58293367HCID 58293367, compound

Product 1

HCID 582933013-Methyl-1,6-diazaspiro[3.4]octane-1-carboxylic acid tert-butyl esterYield 102.1%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of an optically-active compound of 6-benzyl-3-methyl-1,6-diazaspiro[3.4]octane-1-carboxylic acid tert-butyl ester (10.0 g) in tetrahydrofuran/methanol (50 ml/50 ml) was added 20% palladium hydroxide carbon (2.0 g), and the mixture was hydrogenated under 4 atmospheres for 24 hours. The mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to give the titled compound (7.3 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-710611c8847a433e9925e66cbc46a46c
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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