Diisopropylethylamine → (S)-tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)carbamate

HRID 69830

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C:12]([O:15][C:16]([NH:18][C@@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][CH2:20]1)=[O:17])([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C>>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[N:23]1[CH2:22][CH2:21][CH2:20][C@H:19]([NH:18][C:16](=[O:17])[O:15][C:12]([CH3:13])([CH3:11])[CH3:14])[CH2:24]1)([O-:10])=[O:9]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamate

HCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 67499955(S)-tert-butyl (1-(3-nitropyridin-4-yl)piperidin-3-yl)carbamateYield 99%

Procedure

The method of Example 1 was followed using 1 eq each of 4-chloro-3-nitropyridine, (S)-3-N-Boc-amino piperidine and diisopropylethylamine yielding (S)-tert-butyl 1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate, (99%). LCMS (m/z): 323.1 (MH+); LC Rt=2.13 min.

Sources & evidence

ORD record: ord-946709c13b79443e96be0c40a098331a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822497B2

Linked notes

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