Triethylamine → HCID 69743539, compound

HRID 351600Notes

Reaction equation

HRID 351600 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([CH:13]=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[Si:15]([O:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([CH:13]=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22556715HCID 22556715, compound

Product 1

HCID 69743539HCID 69743539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(hydroxymethyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (47 mmol) in dichloromethane (143 mL) at 0° C. was added tert-butyldimethylsilyl chloride (7.63 g, 49.4 mmol), followed by triethylamine (7.92 mL, 56.4 mmol) and dimethylaminopyridine (0.58 g, 4.7 mmol). The reaction was allowed to warm to room temperature and stirred 2 hours. The reaction was quenched with water, extracted with dichloromethane and the combined organics dried over sodium sulfate. The organic phase was concentrated under reduced pressure to provide 5-(tert-butyldimethylsilyloxy-methyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline. This material was treated essentially as described in Preparation II to provide the title compounds.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organics dried over sodium sulfate
  4. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27894dd5d04546bda430a8abcde4867e
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Reaction notes

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