Triphenylphosphine → HCID 59598938, compound

HRID 1360008Notes

Reaction equation

HRID 1360008 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.[CH2:10]([N:17]1[CH2:22][CH:21]=[C:20]([CH2:23]O)[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:10]([N:17]1[CH2:18][CH:19]=[C:20]([CH2:23][O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[I:9])[CH2:21][CH2:22]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 6202344-Chloro-2-iodophenolHCID 5462977Diethyl azodicarboxylateHCID 11264156(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol

Product 1

HCID 59598938HCID 59598938, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-iodo-phenol 4b (20.32 g, 0.08 mol), (1-benzyl-1, 2, 3, 6-tetrahydro-pyridin-4-yl)-methanol (20.5 g, 0.08 mol) and triphenylphosphine (23.58 g, 0.09 mol) in dry THF (150 mL) was added DEAD (17.4 g, 0.09 mol) at 0° C. under nitrogen atmosphere. After addition, the mixture was stirred at room temperature overnight. The mixture was concentrated to dryness and the residue was basified by Na2CO3 solution (10% 100 mL) and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with water (100 mL×2) and brine (200 mL), dried over Na2SO4, concentrated to dryness. The residue was purified by column on silica gel to afford 1-benzyl-4-(4-chloro-2-iodo-phenoxymethyl)-1,2,3,6-tetrahydro-pyridine 4c (30 g, 86%). 1H NMR (400 MHz, CDCl3): δ 7.73 (d, J=2.4 Hz, 1 H), 7.22-7.38 (m, 6 H), 6.70 (d, J=8.8 Hz, 1 H), 5.82 (s, 1 H), 4.43 (s, 2H), 3.63 (s, 2 H), 3.05 (s, 2 H), 2.67 (t, J=5.6 Hz, 2 H), 2.28 (s, 2 H).

Workup

  1. additionAfter addition
  2. concentrationThe mixture was concentrated to dryness
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. washThe combined organic layers were washed with water (100 mL×2) and brine (200 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column on silica gel

Sources & evidence

ORD record
ord-6826c64e2e3c45cba47d5ade4369a2cf
Source dataset
uspto-grants-2011_02
Patent number
US07879834B2

Reaction notes

Loading…