4-Nitrophenyl chloroformate → HCID 52919445, compound

HRID 515314Notes

Reaction equation

HRID 515314 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[Cl:32].[C:33](Cl)(=O)[O:34]C1C=CC([N+]([O-])=O)=CC=1.[NH2:46][CH2:47][C:48]([CH3:51])([OH:50])[CH3:49]>O1CCCC1>[Cl:32][C:3]1[CH:4]=[C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:29])([C:21]([F:22])([F:23])[F:24])[C:25]([F:28])([F:26])[F:27])=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)[CH:30]=[CH:31][C:2]=1[NH:1][C:33]([NH:46][CH2:47][C:48]([OH:50])([CH3:51])[CH3:49])=[O:34]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86670954HCID 86670954, compound

Product 1

HCID 52919445HCID 52919445, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-((4-(4-amino-3-chlorobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.416 mmol, 200 mg) and 4-nitrophenyl carbonochloridate (0.416 mmol, 84 mg) in tetrahydrofuran (5 mL) was stirred at room temperature for 30 minutes. 1-Amino-2-methylpropan-2-ol (0.832 mmol, 0.106 mL, 74.1 mg) was added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue purified by silica column chromatography (eluent: dichloromethane-5% methanol in dichloromethane) to afford the title compound (58.5 mg). MS (ESI) m/z 596.5 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by silica column chromatography (eluent: dichloromethane-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fc43098392be41869c32a909c48bf0c3
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…