1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-Vinyl-tetrahydro-pyran-3-carboxylic acid benzyl ester

HRID 2176258Notes

Reaction equation

HRID 2176258 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([CH:17](OS(C(F)(F)F)(=O)=O)[CH3:18])[CH2:16][CH2:15][CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2>ClCCl>[CH2:1]([O:8][C:9]([C:11]1([CH:17]=[CH2:18])[CH2:16][CH2:15][CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867060993-(1-Trifluoromethanesulfonyloxy-ethyl)-tetrahydro-pyran-3-carboxylic acid benzyl ester

Product 1

HCID 867060983-Vinyl-tetrahydro-pyran-3-carboxylic acid benzyl esterYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(1-trifluoromethanesulfonyloxy-ethyl)-tetrahydro-pyran-3-carboxylic acid benzyl ester (8.368 mmol) in dichloromethane (100 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (5.0 mL, 33.472 mmol). After stirring at room temperature for 2.5 h, the volatiles were removed in vacuo and the residue was purified by silica gel chromatography using a 100 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 4:1 to afford the title compound (809.5 mg, 39% over two steps) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.58-1.80 (m, 3H), 2.29-2.40 (m, 1H), 3.42-3.54 (m, 2H), 3.81 (app dt, J=10.5, 4.2 Hz, 1H), 4.27 (dd, J=11.4, 1.8 Hz, 1H), 5.13-5.27 (m, 4H), 5.77 (dd, J=17.4, 10.9 Hz, 1H), 7.31-7.42 (m, 5H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 4:1

Sources & evidence

ORD record
ord-4d69633a125d40d5ae8f22bd98250e0c
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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