Potassium Carbonate → (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol

HRID 2383074Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:28][C@@H:29]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:30][OH:31].[Cl-].[NH4+]>C(#N)C>[CH:33]1([CH2:32][C@H:29]([NH:28][CH2:2][C:3]([N:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:4])[CH2:30][OH:31])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (12 mg) in acetonitrile (0.5 mL) were added potassium carbonate (3 mg) and (S)-(+)-2-amino-3-cyclohexyl-1-propanol hydrochloride (15 mg), followed by stirring at 80° C. for 4 hours. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction liquid, followed by extraction with chloroform. The solvent was evaporated and the resulting residue was purified by preparative HPLC to obtain (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol (4.1 mg).

Workup

extractionfollowed by extraction with chloroform
customThe solvent was evaporated
customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-310254a4ff5a409fafc0cbb4379920d4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263607B2

Reaction notes

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