Chlorotrimethylsilane → HCID 67253047, compound

HRID 1798033Notes

Reaction equation

HRID 1798033 reaction equation
[CH3:1][Si](Cl)(C)C.Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(OC(N1[CH2:25][CH2:24][CH:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[C:29]([B:35]3[O:39]C(C)(C)C(C)(C)O3)[CH:28]=2)CC1)=O)(C)(C)C.[NH4+].[Cl-].C1C[O:49][CH2:48][CH2:47]1>[Zn]>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][CH:33]1[O:34][B:35]([OH:39])[C:29]2[CH:28]=[C:27]([O:26][CH:23]3[CH2:24][CH2:25][CH2:47][CH2:48][O:49]3)[CH:32]=[C:31]([CH3:1])[C:30]1=2)[CH3:12]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 7748Ethyl bromoacetateHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 59525382HCID 59525382, compound

Product 1

HCID 67253047HCID 67253047, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
55 °C

Procedure

To a suspension of zinc dust (4.41 g, 67.4 mmol) in THF (30 mL) was added trimethylsilyl chloride (1.46 g, 13.5 mmol) at 40° C. The mixture was heated to 55° C. and stirred for 15 minutes. After cooling down to 37° C., ethyl bromoacetate (9.01 g, 53.9 mmol) was slowly added to the reaction mixture at 37-40° C. After addition, the resulting mixture was allowed to cool to room temperature over 30 minutes. This solution was added to a solution of 4-[4-formyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (1.4 g, 3.2 mmol) in THF (10 mL) at −78° C. The mixture was allowed to warm to room temperature over 1.5 hours before treating with saturated NH4Cl (10 mL) and extracting with EtOAc (2×25 mL). The organic extracts were washed with brine, dried and concentrated in vacuo to give the product which was used without further purification.

Workup

  1. temperatureAfter cooling down to 37° C.
  2. additionAfter addition
  3. temperatureto cool to room temperature over 30 minutes
  4. temperatureto warm to room temperature over 1.5 hours
  5. extractionextracting with EtOAc (2×25 mL)
  6. washThe organic extracts were washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto give the product which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-1b498cf529654d848842fecada5f6108
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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