Hydrochloric Acid → (S)-1-[5-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentyl]-3-methyl-piperazin-2-one

HRID 2095495Notes

Reaction equation

C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([N:23]2[CH2:30][CH2:29][C:26]3([CH2:28][CH2:27]3)[C@H:25]([OH:31])[CH2:24]2)=[O:22])[C:13](=[O:32])[C@@H:12]1[CH3:33])=O)C1C=CC=CC=1.Cl>>[OH:31][C@@H:25]1[CH2:24][N:23]([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][NH:11][C@@H:12]([CH3:33])[C:13]2=[O:32])[CH2:30][CH2:29][C:26]21[CH2:28][CH2:27]2

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 67074445(S)-4-[5-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 67074712(S)-1-[5-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentyl]-3-methyl-piperazin-2-oneYield 83%

Procedure

In analogy to intermediate 12E, (S)-4-[5-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester was hydrogenated without aqueous HCl to give the titled compound in 83% yield as light yellow oil. MS: 324.23 (MH+).

Sources & evidence

ORD record: ord-ed86057fed7f4164a5f36ab1405d36ee
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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