2-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline → tert-Butyl cyclopentyl(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)amino)benzyl)carbamate

HRID 1051445Notes

Reaction equation

[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.[NH2:15][C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=1)[CH2:19][N:20]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>CCO>[CH:28]1([N:20]([CH2:19][C:18]2[CH:33]=[CH:34][CH:35]=[C:16]([NH:15][CH2:3][CH:2]([OH:1])[CH2:4][N:5]3[CH2:14][CH2:13][C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:6]3)[CH:17]=2)[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (170 mg, 0.899 mmol) in EtOH (10 mL) was added tert-butyl 3-aminobenzyl(cyclopentyl)carbamate (313 mg, 1.08 mmol) and the solution heated at 100° C. in a sealed tube overnight. The solvent was then evaporated off and the residue purified by prep-TLC to give 100 mg compound as colorless oil (280 mg, 65%). LCMS (m/z): 480.3 (M+1)

Workup

customThe solvent was then evaporated off
customthe residue purified by prep-TLC

Sources & evidence

ORD record: ord-1d5a51df64f84319953dca1808c2d00c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388173B2

Reaction notes

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