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

HRID 2095501Notes

Reaction equation

C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]([CH3:32])([CH3:31])[C:20]([N:22]2[CH2:29][CH2:28][C:25]3([CH2:27][CH2:26]3)[C@H:24]([OH:30])[CH2:23]2)=[O:21])[C:13](=[O:33])[C@@H:12]1[CH3:34])=O)C1C=CC=CC=1.Cl>>[OH:30][C@@H:24]1[CH2:23][N:22]([C:20](=[O:21])[C:19]([CH3:32])([CH3:31])[CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][NH:11][C@@H:12]([CH3:34])[C:13]2=[O:33])[CH2:29][CH2:28][C:25]21[CH2:27][CH2:26]2

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 67074054(S)-4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 67074651(S)-1-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-3-methyl-piperazin-2-oneYield 99%

Procedure

In analogy to intermediate 12E, (S)-4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-3,3-dimethyl-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester was hydrogenated without aqueous HCl to give the titled compound in 99% yield as light yellow oil. MS: 338.24 (MH+).

Sources & evidence

ORD record: ord-fcf58932efbd416f875efb61e4e6554b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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