3-Methoxyphenyl isocyanate → HCID 54596906, compound

HRID 540366Notes

Reaction equation

HRID 540366 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:8]1.CC([O-])(C)C.[Na+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1>C1(C)C=CC=CC=1>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([NH:36][C:37]([N:17]2[CH2:16][CH2:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([N:9]4[CH2:10][CH2:11][C@H:7]([N:3]5[CH2:4][CH2:5][CH2:6][C@@H:2]5[CH3:1])[CH2:8]4)[CH:13]=3)[CH2:18]2)=[O:38])[CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 878433-Methoxyphenyl isocyanateHCID 23676156Sodium t-butoxideHCID 674693316-((2S,3'S)-2-Methyl-[1,3']bipyrrolidinyl-1'-yl)-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 54596906HCID 54596906, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

6-((2S,3′S)-2-Methyl-[1,3′]bipyrrolidinyl-1′-yl)-1,2,3,4-tetrahydro-isoquinoline (100 mg, 0.35 mmol, 1 eq) was dissolved in 3.5 mL of toluene and NaOt-Bu (50 mg, 0.51 mmol, 1.45 eq) was added followed by 3-methoxy phenylisocyanate (50 μL, 0.39 mmol, 1.1 eq). The reaction mixture was stirred at 35° C. for 12 h, where five grams of Celite was added, the mixture was concentrated under vacuum and purified by column chromatography on silica gel (5% MeOH in CH2Cl2; 40 g column; 35 mL/min). This gave 20 mg (13%) of the title compound as an orange semi-solid.

Workup

  1. additionwhere five grams of Celite was added
  2. concentrationthe mixture was concentrated under vacuum
  3. custompurified by column chromatography on silica gel (5% MeOH in CH2Cl2; 40 g column; 35 mL/min)

Sources & evidence

ORD record
ord-b0d3a54c8cb3476d9af27be045d92bcb
Source dataset
uspto-grants-2014_10
Patent number
US08871788B2

Reaction notes

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