Pyrrolidine → HCID 86753685, compound

HRID 361775Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:30])[C:12]([CH3:29])([CH3:28])[CH:13]([CH2:26][CH3:27])[NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][C:17]=2[F:24])[CH2:7][CH2:6]1.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:30])[C:12]([CH3:28])([CH3:29])[CH:13]([CH2:26][CH3:27])[NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[NH:23])=[CH:18][C:17]=2[F:24])[CH2:7][CH2:6]1

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 86753686HCID 86753686, compound

Product 1

HCID 86753685HCID 86753685, compoundYield 21%

Procedure

N-Boc-β-ethyl-α,α-dimethyl-β-alanine was condensed with 4-piperidineacetic acid methyl ester in the same manner as in Example 43 to yield N-(N-β-ethyl-α,α-dimethyl-β-alanyl)-4-piperidineacetic acid methyl ester. From the resulting compound, methyl-N-(N-(4-cyano-2-fluorobenzoyl)-β-ethyl-α,α-dimethyl-β-alanyl)-4-piperidineacetate was derived in the same manner as in Example 45. The same procedure as in Example 45 was performed with this compound (1.0 g, 2.3 mmol) by using pyrrolidine (1.9 ml) as an amine to yield the titled compound (248 mg, 21%).

Sources & evidence

ORD record: ord-3281b5fbbc6a4c989fefe7d42a5af265
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866592

Reaction notes

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