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

HRID 2095584Notes

Reaction equation

HRID 2095584 reaction equation
[Cl:1]C1C=C(N2C=CC(=O)N(CCCC(O)=O)C[C@H]2C)C=CC=1C(F)(F)F.[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

Participants

3

Reactant 2

HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 670747854-[(R)-4-(3-Chloro-4-trifluoromethyl-phenyl)-3-methyl-7-oxo-2,3,4,7-tetrahydro-[1,4]diazepin-1-yl]-butyric acid2×

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-chloro-4-trifluoromethyl-phenyl)-3-methyl-7-oxo-2,3,4,7-tetrahydro-[1,4]diazepin-1-yl]-butyric acid (22% ee) (intermediate 34) and 1.1 eq. of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave after purification by flash chromatography (50 g amine-silica, ethyl acetate/n-heptane 1:1, 4:1, 9:1, 100%, ethyl acetate/ethanol 99:1 to 95:5) 69% of the title compound as off-white foam. MS: 500.19 (MH+, Cl).

Sources & evidence

ORD record
ord-1282685e8c4d4ed09d5c71e4ece470f7
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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