Ethanol → HCID 58232200, compound

HRID 2095581Notes

Reaction equation

HRID 2095581 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([N:19]3[CH2:26][CH2:25][C:22]4([CH2:24][CH2:23]4)[C@H:21]([OH:27])[CH2:20]3)=[O:18])[C:10](=[O:28])[C@@H:9]2[CH3:29])=[CH:4][C:3]=1[O:30][C:31]([F:34])([F:33])[F:32].CCO>CCCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([N:19]3[CH2:26][CH2:25][C:22]4([CH2:24][CH2:23]4)[C@H:21]([OH:27])[CH2:20]3)=[O:18])[C:10](=[O:28])[C@H:9]2[CH3:29])=[CH:4][C:3]=1[O:30][C:31]([F:32])([F:33])[F:34]

Participants

4

Reactant 2

HCID 702EthanolHCID 58232145HCID 58232145, compound

Product 1

HCID 58232200HCID 58232200, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The title compounds were prepared by chiral separation of (S)-4-(4-chloro-3-trifluoromethoxy-phenyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (61% ds) on a Reprosil Chiral NR, (40% EtOH in n-heptane) to give 25% of (R)-4-(4-chloro-3-trifluoromethoxy-phenyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (example 63) as white foam, MS: 504.19 (MH+, Cl) and 33% of (S)-4-(4-chloro-3-trifluoromethoxy-phenyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-3-methyl-piperazin-2-one (example 62) as white foam, MS: 504.19 (MH+, Cl).

Sources & evidence

ORD record
ord-17b17911f5be4a08b08413bf001e1107
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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