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

HRID 2095539Notes

Reaction equation

HRID 2095539 reaction equation
COC(=O)C(N1C(=O)CCN(C(=O)/C=C/C2C=CC=C([Cl:26])C=2)CC1)CC(O)=O.CCN(CC)CC.[CH2:36]1[C:38]2([CH2:43][CH2:42][NH:41][CH2:40][C@H:39]2[OH:44])[CH2:37]1>>[ClH:26].[CH2:37]1[C:38]2([CH2:43][CH2:42][NH:41][CH2:40][C@H:39]2[OH:44])[CH2:36]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 67074404HCID 67074404, compound2×

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-chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 1-methyl ester (intermediate 8) with 1.1 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/MeOH 98:2-95:5), the titled compound in 76% yield as white foam. MS: 518.3 (MH+, 1Cl).

Sources & evidence

ORD record
ord-062999e7638845c496f8285febbfe2a4
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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