Triphenylphosphine → HCID 86627627, compound

HRID 1875550Notes

Reaction equation

HRID 1875550 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42](=[O:47])[C:43]([F:46])([F:45])[F:44])=[C:37]([I:48])[CH:36]=1.[C:49]([O:53][C:54]([N:56]1[CH2:61][CH:60]=[C:59]([CH2:62]O)[CH2:58][CH2:57]1)=[O:55])([CH3:52])([CH3:51])[CH3:50]>O1CCCC1>[C:49]([O:53][C:54]([N:56]1[CH2:57][CH:58]=[C:59]([CH2:62][N:41]([C:38]2[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][C:37]=2[I:48])[C:42](=[O:47])[C:43]([F:45])([F:46])[F:44])[CH2:60][CH2:61]1)=[O:55])([CH3:52])([CH3:50])[CH3:51]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 12129715N-(4-Chloro-2-iodophenyl)-2,2,2-trifluoroacetamideHCID 225944841,1-Dimethylethyl 3,6-dihydro-4-(hydroxymethyl)-1(2H)-pyridinecarboxylate

Product 1

HCID 86627627HCID 86627627, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (5.16 g) was dissolved in tetrahydrofuran (130 ml) and the solution was cooled to 0° C. under argon. Diisopropylazodicarboxylate (3.82 ml) was added dropwise over 10 min and the resulting mixture was stirred at 0° C. for 20 min (formation of a white precipitate). N-(4-Chloro-2-iodo-phenyl)-2,2,2-trifluoro-acetamide (5.5 g) was added as a solid, followed by 4-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 2001, 66, 5545-5551, 3.4 g) dissolved in a minimum volume of tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The solution was then concentrated in vacuo and the residue subjected to silica gel chromatography (cyclohexane:ethyl acetate 9:1) to afford 4-{[(4-chloro-2-iodo-phenyl)-(2,2,2-trifluoro-acetyl)-amino]-methyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (4.7 g). 1H NMR (600 MHz, CDCl3) 1.5 (s, 9H), 2.20 (m, 2H), 3.49 (m, 1H), 3.50 (d, J=17 Hz, 1H), 3.55 (m, 1H), 3.8-3.9 (m, 1H), 5.02 (d, J=17 Hz, 1H), 5.40 (s, 1H), 7.0 (m, 1H), 7.38 (dd, 1H), 7.92 (d, 1H); MS (ES+) 445/447 (M+H+—CO2-isobutene), 486/488 (M+H+-isobutene).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-ae9844d837ba4c6da2603e4c97b93f4e
Source dataset
uspto-grants-2012_11
Patent number
US08309567B2

Reaction notes

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