HCID 117929159, compound → HCID 118377853, compound

HRID 1055561Notes

Reaction equation

HRID 1055561 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH:51]=[O:52])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:53][Mg]Br>O1CCCC1>[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH:51]([OH:52])[CH3:53])[CH2:11][O:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 117929159HCID 117929159, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 118377853HCID 118377853, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carbaldehyde 19b (3 g, 4.15 mmol) in dry tetrahydrofuran (50 mL) was added methylmagnesium bromide (2 mL, 6.22 mmol, 3M in ethyl ether) dropwise at 0° C. The mixture warmed up to room temperature and stirred for 5 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with water (50 mL×2) and then saturated aqueous sodium chloride (50 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 19c as yellow oil (2.16 g, 70.4%).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL)
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. washThe combined organic layers were washed with water (50 mL×2)
  4. dry with materialsaturated aqueous sodium chloride (50 mL×2) in turn, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d2db6e12d32c401ab51e7ec231e0e285
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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