Potassium Carbonate → (3R)-1-[1-(4-Bromophenyl)ethyl]-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]-nonan-6-one

HRID 1672392Notes

Reaction equation

HRID 1672392 reaction equation
[CH:1]1([N:7]2[CH2:16][CH2:15][C:9]3([NH:13][CH2:12][C@H:11]([OH:14])[CH2:10]3)[C:8]2=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS(O[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=1)[CH3:24])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)S(=O)=O>>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([CH:23]([N:13]2[C:9]3([CH2:15][CH2:16][N:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[C:8]3=[O:17])[CH2:10][C@@H:11]([OH:14])[CH2:12]2)[CH3:24])=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 222898561-(4-Bromophenyl)ethyl methanesulfonateHCID 67355529(3R)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-oneHCID 178486088HCID 178486088, compound

Product 1

HCID 24759313(3R)-1-[1-(4-Bromophenyl)ethyl]-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]-nonan-6-one

Conditions

Temperature
100 °C

Procedure

A mixture of (3R)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one (0.030 g, 0.00012 mol; which was prepared by using procedures analogous to those described for the synthesis of Example 32, derived from peak 2 of step 2), 1-(4-bromophenyl)ethyl methanesulfonate (0.053 g, 0.00019 mol) and potassium carbonate (0.035 g, 0.00025 mol) in dimethylsulfonamide (DMSO) (1.0 mL, 0.014 mol) was stirred at 100° C. for 16 h. The crude reaction mixture was purified by prep. HPLC to afford the desired product. LC-MS: 421.0/423.0 (M+1H)+.

Workup

  1. customwhich was prepared
  2. customthose described for the synthesis of Example 32
  3. customThe crude reaction mixture
  4. customwas purified by prep

Sources & evidence

ORD record
ord-6fb3443daec74b119efb9d9c67e125f6
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

Loading…