Tributylstannane → HCID 70296583, compound

HRID 1420678Notes

Reaction equation

[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH2:14]([N:21]1[CH2:26][CH2:25][CH2:24][C:23]([C:28]#[C:29][CH2:30][OH:31])([OH:27])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N1CCCC(C([Sn](CCCC)(CCCC)CCCC)=CCO)(O)C1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:14]([N:21]1[CH2:26][CH2:25][CH2:24][C:23]([CH:28]=[C:29]([Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:1][CH2:2][CH2:3][CH3:4])[CH2:30][OH:31])([OH:27])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: -5 °C

Procedure

Tributyltin hydride (7.8 ml, 29 mmol) was added dropwise to a degassed solution of 1-benzyl-3-(3-hydroxy-1-propyn-1-yl)piperidin-3-ol (Desc. 1; 5.91 g, 24.1 mmol) and tetrakis(trisphenylphosphine)palladium(0) (0.52 g, 0.45 mmol) in toluene (100 ml) at -5° C. The reaction mixture was stirred at -5° C. for 2 hours, allowed to warm up and concentrated in vacuo to afford an approximately 2.5:1 mixture of the title compound and isomeric 1-benzyl-3-(3-hydroxy-1-tributylstannyl-1-propen-1-yl)piperidin-3-ol. The mixture was purified by flash chromatography, eluting with ethyl acetate/hexane (1:2), to give the title compound (8.82 g, 68%; δH (250 MHz, CDCl3) 0.88 (15 H, m), 1.24-1.53 (14H, m), 1.78 (2H, m), 1.98 (1H, m), 2.11 (1H, d, J 11.1Hz), 2.69-2.80 (2H, m), 3.51 (1H, d, J. 13.2Hz, NCHACHBPh), 3.57 (1H, d, J 13.2Hz, NCHACHBPh), 4.44 (2H, br s, CH2OH), 5.38 (1H, br s, CH=C), 7.26-7.34 (5H, m ArH).

Workup

temperatureto warm up
concentrationconcentrated in vacuo
customto afford

Sources & evidence

ORD record: ord-329d0ae8f7d146708f3730d112e850e3
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071928

Reaction notes

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