4'-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-5-chloro-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione → 6-chloro-4'-[5-chloro-2-(4-piperidinyloxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504468Notes

Reaction equation

HRID 504468 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[CH:22]2[CH2:27][C:26](=[O:28])[NH:25][CH:24]([C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=3[CH3:36])[C:23]32[C:44]2[C:39](=[CH:40][C:41]([Cl:45])=[CH:42][CH:43]=2)[NH:38][C:37]3=[O:46])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:45][C:41]1[CH:40]=[C:39]2[NH:38][C:37](=[O:46])[C:23]3([CH:22]([C:16]4[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=4[O:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH2:27][C:26](=[O:28])[NH:25][CH:24]3[C:29]3[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=3[CH3:36])[C:44]2=[CH:43][CH:42]=1

Participants

4

Reactant 1

HCID 749285074'-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-5-chloro-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 749287696-chloro-4'-[5-chloro-2-(4-piperidinyloxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 105.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of racemic (2′S,3S,4′R)-4′-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-5-chloro-phenyl]-6-chloro-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.7 g, 1 mmol) in TFA (10 mL) was stirred at r.t. for 0.5 h. The solution was diluted with DCM, washed with 1N Na2CO3 aq. (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, concentrated to give title compound as a yellow solid (Yield: 0.6 g).

Workup

  1. washwashed with 1N Na2CO3 aq. (50 mL) and brine (50 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6b55f4d974e64fd19ebddca312d0b6fc
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

Loading…