1-Pyrrolidineethanamine → HCID 59772403, compound

HRID 2220210Notes

Reaction equation

HRID 2220210 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[CH2:18][N:17]([C:19](=[O:21])[CH3:20])[C:16]4[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=4[CH2:14][CH2:13][C:12]=3[CH:26]=2)[CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(O[Na])(C)(C)C.[NH2:79][CH2:80][CH2:81][N:82]1[CH2:86][CH2:85][CH2:84][CH2:83]1>C1(C)C=CC=CC=1>[C:19]([N:17]1[CH2:18][C:11]2[CH:10]=[CH:9][C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:79][CH2:80][CH2:81][N:82]4[CH2:86][CH2:85][CH2:84][CH2:83]4)[N:7]=3)=[CH:26][C:12]=2[CH2:13][CH2:14][C:15]2[CH:25]=[CH:24][CH:23]=[CH:22][C:16]1=2)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 634876Binap, (A+-)-HCID 86601524HCID 86601524, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 59772403HCID 59772403, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1-[9-(6-Bromo-pyridin-2-yl)-11,12-dihydro-6H-dibenzo[b,f]azocin-5-yl]-ethanone (prepared according to Example 14 and Example 195 starting from Example 2) (17 mg, 0.04 mmol), BINAP (5 mg, 0.008 mmol), t-BuONa (10 mg, 0.1 mmol) and N-(2-aminoethyl)pyrrolidine (6 μl, 0.05 mmol) in toluene (2 mL) was purged with argon, then heated at 95° C. for 1 h. The reaction mixture was cooled to room temperature, concentrated and purified by preparative reversed-phased HPLC to give the title compound (5.8 mg, 33%). HPLC Rt=1.52(b) min. m/z=441 (M+H+).

Workup

  1. customwas purged with argon
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. custompurified by preparative reversed-phased HPLC

Sources & evidence

ORD record
ord-5bcafc3d3d0e4333b1912ef1baf9540b
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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