(4S)-6-Azaspiro[2.5]octan-4-ol → (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

HRID 2095598Notes

Reaction equation

HRID 2095598 reaction equation
[Cl:1]C1C=[C:4]([N:12]2CCN(C[C@@H](O)CC(O)=O)[C:14](=[O:25])[C@@H:13]2C)[CH:5]=[CH:6][C:7]=1[C:8](F)(F)F.C1C2(CCNC[C@H]2O)C1>>[ClH:1].[CH2:7]1[C:6]2([CH2:5][CH2:4][NH:12][CH2:13][C@H:14]2[OH:25])[CH2:8]1

Participants

3

Reactant 2

HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 67074550(S)-4-[(S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-3-hydroxy-butyric acid2×

Product 1

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

Procedure

In analogy to example 15, (S)-4-[(S)-4-(3-chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-3-hydroxy-butyric acid (61% ds) (intermediate 44) and 1.1 eq. of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave after flash chromatography (SiO2, dichloromethane/methanol 2%) and precipitation (dichloromethane/n-pentane) the titled compound in 61% yield (80% ds) as white powder. MS: 504.19 (MH+, 1Cl).

Sources & evidence

ORD record
ord-ac6206c61da54ff5a663b7a44aa66e9e
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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