HCID 21193082, compound → HCID 131722698, compound

HRID 1068187Notes

Reaction equation

[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:16])[CH2:4]1)=O.Cl.[CH:34]1[C:39]2[CH2:40][CH2:41][N:42]([CH:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)[C:43](=[O:45])[O:44][C:38]=2[CH:37]=[CH:36][CH:35]=1>>[CH:34]1[C:39]2[CH2:40][CH2:41][N:42]([CH:46]3[CH2:51][CH2:50][N:49]([CH2:1][C@@H:3]4[C@@H:7]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)[CH2:6][N:5]([C@H:14]([CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]5)[C:15]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=5)=[O:16])[CH2:4]4)[CH2:48][CH2:47]3)[C:43](=[O:45])[O:44][C:38]=2[CH:37]=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 21193082HCID 21193082, compound

HCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 131722698HCID 131722698, compoundYield 76%

Procedure

The title compound (36 mg) was prepared by reductive amination of 31 mg of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)- cyclohexaneacetic acid, 4-methoxybenzyl ester (prepared above as Aldehyde 5) with 22 mg of 4-(8,9-dihydro-7H-5-oxa-7-aza-benzocyclo-hepten-6-one-7-yl)-piperidine hydrochloride according to the procedure of Example 1, step D. 1H NMR (500MHz, CDCl3): δ0.9-1.3 (m, 5H), 1.5-2.0 (m, 12H), 2.25-3.3 (m, 13H), 3.63 (m, 2H), 3.82 (s, 3H), 3.96 (m, 1H), 5.13 (ABq, 2H), 6.9-7.4 (m, 13H).

Sources & evidence

ORD record: ord-826b09c6f53941c188f3f683fe12f2ee
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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