Lithium iodide → HCID 59279488, compound

HRID 1098142Notes

Reaction equation

HRID 1098142 reaction equation
[I-].[Li+].[Si:3]([O:10][C@@H:11]([CH2:16][O:17][CH:18]1[CH2:21][CH2:20][CH2:19]1)[C:12]([O:14]C)=[O:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C(OCC)(=O)C>[Si:3]([O:10][C@@H:11]([CH2:16][O:17][CH:18]1[CH2:21][CH2:20][CH2:19]1)[C:12]([OH:14])=[O:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 59279519HCID 59279519, compound

Product 1

HCID 59279488HCID 59279488, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
75 °C

Procedure

Lithium iodide (1.986 g, 14.84 mmol) was added to (S)-methyl 2-(tert-butyldimethylsilyloxy)-3-cyclobutoxypropanoate (Intermediate R3) (1.07 g, 3.71 mmol) in ethyl acetate (15 mL). The resulting suspension was protected from light and stirred at reflux (75° C.) for 6 hours. The reaction mixture was diluted with ethyl acetate (75 mL) washed sequentially with 1M sodium metabisulphite (25 mL), water (25 mL) and saturated brine (25 mL). The organic layer was dried (MgSO4) and evaporated to afford the crude product (0.920 g, 90%) that was used without further purification. 1H NMR (400 MHz, DMSO) δ 0.09 (d, 6H), 0.91 (s, 9H), 1.40-1.54 (m, 1H), 1.59-1.71 (m, 1H), 1.75-1.90 (m, 2H), 2.10-2.22 (m, 2H), 3.40-3.57 (m, 2H), 3.90-4.02 (m, 1H), 4.25-4.31 (m, 1H), 12.55 (s, 1H); m/z (EI+) M+=274; GC tR=11.09 min.

Workup

  1. washwashed sequentially with 1M sodium metabisulphite (25 mL), water (25 mL) and saturated brine (25 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-afc1f43d653347499ea4f2ef4906d04d
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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