Isopropyl iodide → (+/-)-cis-1-Methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate

HRID 1587156Notes

Reaction equation

HRID 1587156 reaction equation
[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([OH:15])=[O:14])[CH2:5]1)#[N:2].[CH3:16][CH2:17][CH2:18]CCCC=CCCC.IC(C)C>C(#N)C.C(OCC)C>[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([O:15][CH:17]([CH3:18])[CH3:16])=[O:14])[CH2:5]1)#[N:2]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 136496Undec-4-eneHCID 10976794[(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid

Product 1

HCID 10999646(+/-)-cis-1-Methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (±)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 0.6 g (3 mmol), in acetonitrile, 2 mL, is added 1,8-diazabicyclo5.4.0]-undec-7-ene (DBU), 0.45 mL (3 mmol), and 2-iodopropane, 0.33 mL (3.3 mmol). The solution is stirred overnight at room temperature, diluted with diethyl ether, washed with brine, and dried (magnesium sulfate). Flash chromatography provides 0.55 g of (±)-cis-1-methylethyl 6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetate.

Workup

  1. washwashed with brine
  2. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-57499197f07745e7b7cb795561cbd394
Source dataset
uspto-grants-1993_06
Patent number
US05216174

Reaction notes

Loading…