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

HRID 2095538Notes

Reaction equation

HRID 2095538 reaction equation
COC(=O)C(N1C(=O)CCN(C(=O)/C=C/C2C=CC([Cl:26])=C(Cl)C=2)CC1)CC(O)=O.CCN(CC)CC.[CH2:37]1[C:39]2([CH2:44][CH2:43][NH:42][CH2:41][C@H:40]2[OH:45])[CH2:38]1>>[ClH:26].[CH2:38]1[C:39]2([CH2:44][CH2:43][NH:42][CH2:41][C@H:40]2[OH:45])[CH2:37]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 670740782-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 1-methyl ester2×

Product 1

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

Procedure

In analogy to the procedure described in example 6A, 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 1-methyl ester (intermediate 7) with 1.5 eq. of Et3N (added before cooling) and 1.05 eq. of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave, after purification on a SiO2-column (dichloromethane/Isopropanol 97.5:2.5-9:1 gradient), the titled compound in 33% yield as white foam. MS: 552.0 (MH+, 2Cl).

Sources & evidence

ORD record
ord-f5eae9c69043424db6517d803e3cccc7
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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