Ethyl 4-piperidinecarboxylate → HCID 67547473, compound

HRID 490622Notes

Reaction equation

HRID 490622 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([N:13](C(OC(C)(C)C)=O)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:10][CH:9]1[C:30](O)=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:35][C:36]([CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:37])[CH3:34]>>[CH2:33]([O:35][C:36]([CH:39]1[CH2:38][CH2:43][CH2:42][N:41]([C:30]([C@@H:9]2[CH2:10][C@H:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[CH2:12][N:8]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:31])[CH2:40]1)=[O:37])[CH3:34].[CH2:33]([O:35][C:36]([CH:38]1[CH2:43][CH2:42][N:41]([C:30]([C@@H:9]2[CH2:10][C@H:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=3[F:22])[CH2:12][N:8]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:31])[CH2:40][CH2:39]1)=[O:37])[CH3:34]

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 675474701-Benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid

Product 2

HCID 67547473HCID 67547473, compoundYield 14%HCID 67547961HCID 67547961, compound

Procedure

As described for Example 1f, 1-benzyl-4-[tert-butoxycarbonyl-(2,4-difluoro-benzyl)-amino]-pyrrolidine-2-carboxylic acid (60.0 mg, 0.134 mmol) was converted, using piperidine-4-carboxylic acid ethyl ester instead of 2-piperazin-1-yl-benzonitrile, to the title product [(2S,4S)-1-benzyl-4-(2,4-difluoro-benzylamino)-pyrrolidine-2-carbonyl]-piperidine-3-carboxylic acid ethyl ester (8.7 mg, 14% yield) as colorless oil. MS m/e=486.6 [M+H]+.

Sources & evidence

ORD record
ord-db916c13618841dcb96561ac4d3fc973
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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