Triphenylphosphine → Dimethyl-(4-{4-[2-(1-methylpyrrolidin-2-yl)ethoxy]phenyl}-tetrahydropyran-4-ylmethyl)amine

HRID 272855

Reaction equation

HRID 272855 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:3].[CH3:18][N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[CH2:24][CH2:25]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(OCC)(=O)C.CCCCCCC.C1COCC1>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:25][CH2:24][CH:20]3[CH2:21][CH2:22][CH2:23][N:19]3[CH3:18])=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 933631-Methyl-2-pyrrolidineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol

Product 1

HCID 23091668Dimethyl-(4-{4-[2-(1-methylpyrrolidin-2-yl)ethoxy]phenyl}-tetrahydropyran-4-ylmethyl)amineYield 27.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (405 mg, 1.72 mmol), 2-(1-methyl-pyrrolidin-2-yl)-ethanol (178 mg, 1.38 mmol), PPh3 (451 mg, 1.72 mmol), THF (8 ml) and DIAD (348 mg, 1.72 mmol) were reacted together according to general procedure C. The crude product was subjected to chromatography on alumina eluting with ethyl acetate:heptane (50:50) to provide the title compound (130 mg, 27%) as a colourless oil. 1H NMR (400 MHz, CDCl3) δ7.21 (d, 2H), 6.87 (d, 2H), 4.09-3.95 (m, 2H), 3.75 (dt, 2H), 3.55 (td, 2H), 3.09 (m, 1H), 2.40 (s, 2H), 2.35 (s, 3H), 2.30-1.99 (m, 6H), 1.96 (s, 6H), 1.93-1.63 (m, 6H).

Sources & evidence

ORD record
ord-c7111172352f4bf3bcd314fcdbde6536
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Linked notes

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