Triphenylphosphine → HCID 23091684, compound

HRID 272852Notes

Reaction equation

HRID 272852 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].[N:18]1([CH2:23][CH2:24][CH:25](O)[CH3:26])[CH2:22][CH2:21][CH2:20][CH2:19]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:3][N:2]([CH3:1])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:25]([CH3:26])[CH2:24][CH2:23][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 230916214-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenolHCID 23091639HCID 23091639, compound

Product 1

HCID 23091684HCID 23091684, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Dimethylaminomethyl-tetrahydro-pyran-4-yl)-phenol (1.03 g, 4.40 mmol), 4-pyrrolidin-1-yl-butan-2-ol (0.5 g, 3.50 mmol), PPh3 (1.15 g, 4.40 mmol), THF (10 ml) and DIAD (0.86 ml, 4.40 mmol) were reacted together according to general procedure C. The crude product was purified by preparative HPLC, eluting with acetonitrile/water/0.1% TFA as a gradient, to give the title compound as a yellow oil (125 mg, 10%). 1H NMR (400 MHz, CDCl3) δ7.19 (d, 2H), 6.86 (d, 2H), 4.43 (m, 1H), 3.75 (dt, 2H), 3.60-3.51 (m, 2H), 2.67-2.46 (m, 6H), 2.40 (s, 2H), 2.14-2.04 (m, 2H), 1.97 (s, 6H), 1.93-1.73 (m, 8H), 1.31 (d, 3H).

Workup

  1. customThe crude product was purified by preparative HPLC
  2. washeluting with acetonitrile/water/0.1% TFA as a gradient

Sources & evidence

ORD record
ord-2795e3abbcbf48198d1df2e162bd1662
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

Loading…