1-Bromopropane → HCID 12343450, compound

HRID 271588Notes

Reaction equation

HRID 271588 reaction equation
C(OC([N:11]1[CH2:22][CH2:21][C:14]2([O:18][C:17](=[O:19])[NH:16][C:15]2=[O:20])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32]>CS(C)=O>[CH2:30]([N:16]1[C:15](=[O:20])[C:14]2([CH2:13][CH2:12][NH:11][CH2:22][CH2:21]2)[O:18][C:17]1=[O:19])[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 59834661HCID 59834661, compound

Product 1

HCID 12343450HCID 12343450, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,4-dioxo-1-oxa-3,8-diaza-spiro[4.5]decane-8-carboxylic acid benzyl ester (24.4 g, 80 mmol) in DMSO (240 ml), potassium carbonate (16.5 g, 120 mmol) and bromopropane (11 ml, 120 mmol) are added to the mixture at ambient temperature. The reaction mixture is stirred at ambient temperature for 12 h, quenched with water and extracted with AcOEt:ether (1:1 (v/v)). The combined extracts are washed with brine, dried over magnesium sulfate, filtrated and concentrated. The residue is purified by column chromatography on silica gel using n-hexane:AcOEt=2:1 (v/v). to give 21.2 g of desired product in 76% yield. Rf=0.8 (n-hexane:AcOEt=1:1). To white solid (21.2 g) and 10% Pd/C (3 g), MeOH (300 ml) is added. The reaction mixture is stirred at ambient temperature for 18 h under H2. After the filtration, the solvent is evaporated down to give the desired product.

Workup

  1. customquenched with water
  2. extractionextracted with AcOEt:ether (1:1 (v/v))
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-655622e323704f7ea86b2149ec7ec2e0
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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