2-Amino-2-methyl-1-propanol → 2-Amino-2-methylpropyl 4-((1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)methyl)phenylcarbamate

HRID 515283Notes

Reaction equation

HRID 515283 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][CH:3]=1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.[NH2:45][C:46]([CH3:50])([CH3:49])[CH2:47][OH:48]>ClCCl>[F:24][C:21]([F:22])([F:23])[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[O:48][CH2:47][C:46]([NH2:45])([CH3:50])[CH3:49])=[CH:31][CH:30]=3)[CH2:12][CH2:11]2)=[CH:15][CH:16]=1)([OH:29])[C:25]([F:28])([F:26])[F:27]

Participants

5

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 821294-Nitrophenyl chloroformateHCID 86670937HCID 86670937, compound

Product 1

HCID 866709402-Amino-2-methylpropyl 4-((1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)methyl)phenylcarbamateYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-((4-(4-Aminobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.448 mmol, 200 mg) and 4-nitrophenyl carbonochloridate (0.448 mmol, 90 mg) were combined and stirred in dichloromethane at room temperature for 30 minutes. 2-Amino-2-methylpropan-1-ol (0.896 mmol, 114 μl, 80 mg) was added and the reaction stirred at room temperature overnight. The reaction mixture was concentrated and purified by basic prep-HPLC to give the title compound (94.7 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by basic prep-HPLC

Sources & evidence

ORD record
ord-7b81fd47de0f41639a60a6e83bb6241c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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