Diisopropylethylamine → tert-butyl (3S)-4-[2-(3-cyano-4-methoxy-2-methylphenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 1502016Notes

Reaction equation

HRID 1502016 reaction equation
Br[CH2:2][C:3]([C:5]1[C:6]([CH3:15])=[C:7]([C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)[C:8]#[N:9])=[O:4].[OH:16][CH2:17][C@H:18]1[NH:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1.CCN(C(C)C)C(C)C>C1COCC1>[C:8]([C:7]1[C:6]([CH3:15])=[C:5]([C:3](=[O:4])[CH2:2][N:23]2[CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:19][C@H:18]2[CH2:17][OH:16])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14])#[N:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 895250263-(Bromoacetyl)-6-methoxy-2-methylbenzonitrile

Product 1

HCID 131734292tert-butyl (3S)-4-[2-(3-cyano-4-methoxy-2-methylphenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 3-(bromoacetyl)-6-methoxy-2-methylbenzonitrile (2.25 g, 8.40 mmol) in THF was added tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate (2.18 g, 10.8 mmol) and Hunig's Base (2.93 mL, 16.8 mmol). The reaction was allowed to stir at RT for 16 hours. TLC showed good reaction at that point. The crude reaction was adsorbed onto silica gel, and purified by silica gel flash chromatography to afford the title compound.

Workup

  1. customreaction at that point
  2. customThe crude reaction
  3. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-f99eb5a248a1427eaf19192e7fcb8c33
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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