Triethylamine → HCID 69084009, compound

HRID 1525887Notes

Reaction equation

HRID 1525887 reaction equation
[NH2:1][C:2]1([CH2:5][OH:6])[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C)C1C=CN=CC=1.ClCCl>[Si:15]([O:6][CH2:5][C:2]1([NH2:1])[CH2:4][CH2:3]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 14146220(1-Aminocyclopropyl)methanol

Product 1

HCID 69084009HCID 69084009, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (1-aminocyclopropyl)methanol (9.69 mmol), 4-(dimethylamino)pyridine (0.484 mmol), and triethylamine (21.32 mmol) in anhydrous dichloromethane (25 mL) was added chloro(1,1-dimethylethyl)dimethylsilane (10.66 mmol). After stirring 20 h, the reaction was quenched with saturated aq ammonium chloride and extracted with dichloromethane. The extracts were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to afford the crude title compound (1.70 g, 78% yield) as a colorless liquid. MS(ES)+ m/e 202.2 [M+H]+.

Workup

  1. customthe reaction was quenched with saturated aq ammonium chloride
  2. extractionextracted with dichloromethane
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd0c111c2e60406fb8b987d1e7d71068
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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