Isobutyraldehyde → 7-(2-Chlorophenyl)-1-isobutyl-1,7-diazaspiro[4.4]nonan-6-one

HRID 1672378Notes

Reaction equation

HRID 1672378 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:16][CH2:15][C:10]2([NH:14][CH2:13][CH2:12][CH2:11]2)[C:9]1=[O:17].[CH:18](=O)[CH:19]([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:16][CH2:15][C:10]2([N:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12][CH2:11]2)[C:9]1=[O:17]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 589483317-(2-Chlorophenyl)-1,7-diazaspiro[4.4]nonan-6-one

Product 1

HCID 166550297-(2-Chlorophenyl)-1-isobutyl-1,7-diazaspiro[4.4]nonan-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(2-Chlorophenyl)-1,7-diazaspiro[4.4]nonan-6-one (20 mg, 0.00008 mol) was dissolved in anhydrous DCM (2 mL). To this mixture was added isobutyraldehyde (8.0 μL, 0.000088 mol) and sodium triacetoxyborohydride (3.0E1 mg, 0.00014 mol). The resulting solution was stirred at RT for 16 h. The volatiles were removed in vacuo and the resulting residue was dissolved in acetonitrile/H2O and purified by prep.-LC/MS chromatography to afford the desired product. LC-MS: 307.1 (M+1H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in acetonitrile/H2O
  3. custompurified by prep.-LC/MS chromatography

Sources & evidence

ORD record
ord-8c5223cd1979476598927ad65121b715
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

Loading…