Ethyl (3S)-piperidine-3-carboxylate → HCID 25211913, compound

HRID 1409838Notes

Reaction equation

HRID 1409838 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[C:4]=1[CH3:16].[NH:19]1[CH2:29][CH2:28][CH2:27][C@H:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20]1>>[CH2:25]([O:24][C:22]([C@H:21]1[CH2:27][CH2:28][CH2:29][N:19]([C:13]([C:11]2[S:12][C:8]([C:5]3[C:4]([CH3:16])=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20]1)=[O:23])[CH3:26]

Participants

3

Reactant 2

HCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 25211913HCID 25211913, compound

Procedure

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and (S)-(+)-nipecotic acid, ethyl ester (TCI America, Portland Oreg., USA) by the method described in Example 2 Method B. Colorless solid (415 mg, 91%). 1H NMR (CDCl3) 1.19 (t, J=7.0, 3H), 1.50-1.60 (m, 1H), 1.66-1.82 (m, 2H), 2.02-2.12 (m, 1H), 2.29 (d, J=1.4, 3H), 2.46-2.56 (m, 1H), 3.13 (t, J=11.0, 1H), 3.28 (br s, 1H), 4.08 (q, J 7.0, 3H), 4.10 (obs m, 1H), 4.34 (br s, 1H), 7.28 (d, J=4.0, 1H), 7.39 (d, J=3.5, 1H). 19F NMR −63.12. LC/MS 6.74 min, [M+1]+ 417.

Workup

  1. customLC/MS 6.74 min, [M+1]+ 417

Sources & evidence

ORD record
ord-001e7cb2a7d14085a90f31abeb6abcf1
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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