Pyrrolidine → HCID 11591451, compound

HRID 1661532Notes

Reaction equation

HRID 1661532 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[C@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][C@@H:13]([OH:22])[C@@:12]2([OH:23])[C:11]2[C:24]([O:31][CH2:32][CH3:33])=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[CH:27][C:10]=2[O:9]3)=[CH:4][CH:3]=1.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:29]([O:28][C:26]1[CH:25]=[C:24]([O:31][CH2:32][CH3:33])[C:11]2[C@:12]3([OH:23])[C@H:13]([OH:22])[CH2:14][C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@:8]3([C:5]3[CH:4]=[CH:3][C:2]([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:7][CH:6]=3)[O:9][C:10]=2[CH:27]=1)[CH3:30]

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57545194HCID 57545194, compound

Product 1

HCID 11591451HCID 11591451, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

51.1 mg (0.10 mmol) of (1R*,3S*,3aR*,8bS*)-3a-(4-bromophenyl)-6,8-diethoxy-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1,8b-(1H)-diol (Example 8A), 4.7 mg (0.07 mmol) of pyrrolidine, 7.1 mg (0.07 mmol) of sodium tert-butoxide, 1.2 mg (0.001 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 1.7 mg (0.003 mmol) of rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl are heated in 0.6 ml of toluene at 80° C. under argon overnight. The mixture is then concentrated, taken up in DMSO and filtered, and the filtrate is purified by preparative HPLC. 14.5 mg (43% of theory) of the product are obtained.

Workup

  1. concentrationThe mixture is then concentrated
  2. filtrationfiltered
  3. customthe filtrate is purified by preparative HPLC
  4. custom14.5 mg (43% of theory) of the product are obtained

Sources & evidence

ORD record
ord-35fb74daefa544dbbeb4fc3e86952d52
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

Loading…