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

HRID 2095596Notes

Reaction equation

HRID 2095596 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[CH2:10][C@H:9]2[CH3:22])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24].[CH2:27]1[C:29]2([CH2:34][CH2:33][NH:32][CH2:31][C@H:30]2[OH:35])[CH2:28]1>>[ClH:1].[CH2:28]1[C:29]2([CH2:34][CH2:33][NH:32][CH2:31][C@H:30]2[OH:35])[CH2:27]1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][C:19]([N:32]3[CH2:33][CH2:34][C:29]4([CH2:27][CH2:28]4)[C@H:30]([OH:35])[CH2:31]3)=[O:20])[CH2:10][C@H:9]2[CH3:22])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24]

Participants

4

Reactant 2

HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 67074307HCID 67074307, compound2×

Product 2

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochlorideHCID 58232195HCID 58232195, compound

Procedure

In analogy to the procedure described for example 15, 4-[(R)-4-(4-chloro-3-trifluoromethyl-phenyl)-3-methyl-7-oxo-2,3,4,7-tetrahydro-[1,4]diazepin-1-yl]-butyric acid (46% ee) (intermediate 35) and (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave the title compound in 69% yield as light yellow oil. MS: 544.19 (M+HCOO−, Cl).

Sources & evidence

ORD record
ord-d5432005d33f4b378468096be011a619
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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