(3S)-pyrrolidin-3-ol → HCID 58464886, compound

HRID 2089360Notes

Reaction equation

HRID 2089360 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[OH:11][C@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1>>[CH3:7][N:6]1[C:2]([N:14]2[CH2:15][CH2:16][C@H:12]([OH:11])[CH2:13]2)=[C:3]([N+:8]([O-:10])=[O:9])[CH:4]=[N:5]1

Participants

3

Reactant 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 123448365-chloro-1-methyl-4-nitro-1H-pyrazole

Product 1

HCID 58464886HCID 58464886, compoundYield 96%

Procedure

Following Example 231, 5-Chloro-1-methyl-4-nitro-1H-pyrazole and (S)-(−)-3-hydroxypyrrolidine gave (S)-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)pyrrolidin-3-ol (250 mg, 96%). 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 4.64-4.59 (m, 1H), 3.78 (s, 3H), 3.71-3.59 (m, 2H), 3.39 (td, J=8.8, 3.4 Hz, 1H), 3.24 (dt, J=10.2, 1.6 Hz, 1H), 2.34-2.23 (m, 1H), 2.14-2.04 (m, 2H)

Sources & evidence

ORD record
ord-0ca5de9a1fee4ea5a28bff79a04a10b2
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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