Tributylstannane → HCID 70228035, compound

HRID 1420805Notes

Reaction equation

HRID 1420805 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]([C:15]#[C:16][C:17]([O:19]CC)=O)([OH:14])[C@@H:9]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([SnH:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]2([O:14][C:17](=[O:19])[C:16]([Sn:32]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:15]2)[C@@H:9]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 57264429HCID 57264429, compound

Product 1

HCID 70228035HCID 70228035, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of (2S,3R)-ethyl 3-(1-tert-butoxycarbonyl-3-hydroxy-2-phenylpiperidin-3-yl)propynoate (Description 9, 524 mg, 1.4 mmol) and tetrakis(triphenylphosphine)palladium (0) (50 mg) in toluene (10 ml) was degassed with nitrogen for 30 min. Tributyl tin hydride (0.405 mM, 1.5 mmol) was added dropwise and the resulting mixture was stirred at 23° C. for 2 h. The solvent was evaporated under reduced pressure and the residue was taken up in ethyl acetate (50 ml). The mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml), dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the title compound as a gum (538 mg, 0.87 mmol, 62%). 1H NMR (250 MHz, CDCl3) δ7.63 (1H, s), 7.30 (5H, m), 5.11 (1H, m, 310 (1H, m) 2.19 (1H, m), 1.80 (3H, m), 1.30-150 (12H, m), 1.40 (9H), s), 1.02 (6H), m), and 0.88 (9H), t, J 7.22 Hz), m/z (ES+) 619 (M+1)

Workup

  1. customwas degassed with nitrogen for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. washThe mixture was washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-4ec76da4a6ce4239a501db9870356197
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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