Triphenylphosphine → HCID 18782723, compound

HRID 1420679Notes

Reaction equation

HRID 1420679 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([N:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH:27]=[C:28]([Sn:31]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:29][OH:30])(O)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([N:20]1[CH2:25][CH2:24][CH2:23][C:22]2([O:30][CH2:29][C:28]([Sn:31]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:27]2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70296583HCID 70296583, compound

Product 1

HCID 18782723HCID 18782723, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicaboxylate (3.1 ml, 19.7 mmol) was added dropwise to a solution of 1-benzyl-3-(3-hydroxy-2-tributylstannyl-1-propen-1-yl)piperidin-3-ol (Desc. 2; 8.72 g, 16.26 mmol) and triphenylphosphine (5.12 g, 19.5 mmol) in tetrahydrofuran (100 ml) at -5° C. The cooling bath was removed and the reaction mixture stirred for 45 minutes. The solvent was evaporated, the residue dissolved in acetonitrile (300 ml) and extracted with hexane (3×150 ml). The combined hexane extracts were evaporated and the residue chromatographed on silica, eluting with ethyl acetate/hexane (1:9 then 1:4), to afford the title compound as a colourless oil (5.00 g, 59%); δH (250 MHz, CDCl3) 0.87-0.96 (15 H, m), 1.25-1.35 (6H, m), 1.45-1.60 (11H, m), 1.79 (1H, m), 2.29-2.48 (4H, m), 3.48 (1H, d, J 13.3Hz, NCHZCHBPh), 3.59 (1H, d, J 13.3Hz, NCHACHBPh), 4.67 (2H, m, 2-CH2), 6.03 (1H, br s, 4-CH=), 7.22-7.30 (5H, m ArH).

Workup

  1. customThe cooling bath was removed
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in acetonitrile (300 ml)
  4. extractionextracted with hexane (3×150 ml)
  5. customThe combined hexane extracts were evaporated
  6. customthe residue chromatographed on silica
  7. washeluting with ethyl acetate/hexane (1:9

Sources & evidence

ORD record
ord-a35069340bed4ef9b73c74ff3da339ec
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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