Triethylamine → HCID 10081656, compound

HRID 2407727Notes

Reaction equation

HRID 2407727 reaction equation
[CH2:1]([OH:6])[CH2:2][C@H:3]([OH:5])[CH3:4].[C:7]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[Si:11]([O:6][CH2:1][CH2:2][C@H:3]([OH:5])[CH3:4])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 637497(-)-1,3-Butanediol

Product 1

HCID 10081656HCID 10081656, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(R)-Butane-1,3-diol (5.00 mL), tert-butylchlorodimethylsilane (8.82 g), N,N-dimethylpyridin-4-amine (0.34 g) and triethylamine (23.2 mL) were suspended in dichloromethane (60 mL) and stirred at room temperature overnight. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organics were dried over magnesium sulfate and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 5-10% ethyl acetate/hexane) to furnish to afford the title compound (8.33 g) having the following physical properties.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude material, which
  5. customwas purified by flash column chromatography (eluant: 5-10% ethyl acetate/hexane)
  6. customto furnish

Sources & evidence

ORD record
ord-2c279644a17945adaf323063a48d2a7e
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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