Aluminium lithium hydride → racemic (2'R,3S,4'R)-6-chloro-4'-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)-phenyl]-2'-(2,5-difluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728176Notes

Reaction equation

HRID 1728176 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27](OCC)=[O:28])([CH3:26])[CH3:25])[CH2:14][C:13](=[O:32])[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[F:40])[C:5]2=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH3:25])([CH3:26])[CH2:27][OH:28])[CH2:14][C:13](=[O:32])[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[F:40])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 76568094racemic (2'R,3S,4'R)-6-chloro-4'-[5-chloro-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl]-2'-(2,5-difluoro phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 76567894racemic (2'R,3S,4'R)-6-chloro-4'-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)-phenyl]-2'-(2,5-difluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 3.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 231, racemic (2′R,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(2,5-difluoro phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (200 mg, 0.33 mmol) was reacted with LiAlH4 (63 mg, 1.66 mmol) in THF and the crude product was purified by Prep-HPLC to give title compound as a white solid (6 mg).

Workup

  1. customthe crude product was purified by Prep-HPLC

Sources & evidence

ORD record
ord-dcc48893e0524de7ae1bbd97f6348b70
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…