Water → 4-[(1-Tributylstannyl-2-naphthalenyl) methoxy]piperidine

HRID 580920Notes

Reaction equation

Cl.Br[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CCCCCC.[CH2:27]([Sn:31](Cl)([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30].O>C1COCC1>[CH2:36]([Sn:31]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:32][CH2:33][CH2:34][CH3:35])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH2:37][CH2:38][CH3:39]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 1 (0.5 g, 1.6 mmole) in dry THF (50 ml) was cooled to -70° C. under argon. This was followed by the addition of 2.5 M solution of n-butylithiumin hexane (0.8 ml, 2.1 mmole) and tributyltin chloride (1.7 g, 5 mmole) and the reaction mixture was stirred for 30 min at -70° C. and then for 1 hr at room temperature. The rations mixture was then added to 50 ml of water and extracted with methylene chloride. The methylene chloride fractions were washed with saturated solution of NaHCO3, H2O, brine, dried with anhydrous MgSO4 and evaporated in vacuo to give 64 as light semi-solid. A single component was detected by TLC (ammonium hydroxide/methanol/ethyl acetate/hexane; 1:1:8:2) Rf, 0.5; NMR (CDCl3) d 0.8-1.5 (m, 27H, 3× n-butyl); d 4.6 (s, --CH--O-ring); d 7.8-8.0 (m, 6H, naphthyl).

Workup

waitfor 1 hr at room temperature
extractionextracted with methylene chloride
washThe methylene chloride fractions were washed with saturated solution of NaHCO3, H2O, brine
dry with materialdried with anhydrous MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-f2b6fc29b35943978435f1f0e7686cb7
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05919797

Reaction notes

Loading…