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

HRID 2095577Notes

Reaction equation

HRID 2095577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2CCN(CCCC(O)=O)[C:11](=[O:21])[C@H:10]2C)C=[CH:6][C:7]=1Cl.C1C2(CCNC[C@H]2O)C1>>[ClH:1].[CH2:7]1[C:2]2([CH2:3][CH2:4][NH:9][CH2:10][C@H:11]2[OH:21])[CH2:6]1

Participants

3

Reactant 2

HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 670745604-[(R)-4-(3,4-Dichloro-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-butyric acid

Product 1

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

Procedure

In analogy to the procedure described in Example 15, 4-[(R)-4-(3,4-dichloro-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-butyric acid (62% ee) and 1.1 eq. of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave after precipitation (Et2O/n-pentane) the titled compound in 77% yield as light yellow foam. MS: 454.16 (MH+, 2Cl).

Sources & evidence

ORD record
ord-453a6b42100d41b691c80cca9554a80d
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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