Ethanol → HCID 58232173, compound

HRID 2095579Notes

Reaction equation

HRID 2095579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]([N:23]3[CH2:30][CH2:29][C:26]4([CH2:28][CH2:27]4)[C@H:25]([OH:31])[CH2:24]3)=[O:22])[C:14](=[O:32])[C@@H:13]2[CH3:33])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CCO>CCCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]([N:23]3[CH2:30][CH2:29][C:26]4([CH2:27][CH2:28]4)[C@H:25]([OH:31])[CH2:24]3)=[O:22])[C:14](=[O:32])[C@H:13]2[CH3:33])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

4

Reactant 2

HCID 702EthanolHCID 52913247HCID 52913247, compound

Product 1

HCID 58232173HCID 58232173, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The title compounds were prepared by chiral separation of (S)-4-(3-chloro-4-trifluoromethyl-phenyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (63% ds) on a Reprosil Chiral NR, (40% EtOH in n-heptane) to give 27% of (R)-4-(3-chloro-4-trifluoromethyl-phenyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (example 61) as off-white foam, MS: 488.19 (MH+, Cl) and 42% of (S)-4-(3-chloro-4-trifluoromethyl-phenyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (example 60) as off-white foam, MS: 488.19 (MH+, Cl).

Sources & evidence

ORD record
ord-7b87ad90f60640c3bca85bc59c99ec9c
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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