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Triethylamine → (R)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one

HRID 1666138
Notes
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Reaction equation

HRID 1666138 reaction equation
[OH:1][C@H:2]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6](=[O:13])[CH2:5][CH2:4][CH2:3]1.[Si:14](OS(C(F)(F)F)(=O)=O)([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16].CCN(CC)CC>C(Cl)Cl>[CH:15]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[O:1][C@H:2]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6](=[O:13])[CH2:5][CH2:4][CH2:3]1)([CH3:17])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 57911428(9R)-6,7,8,9-Tetrahydro-9-hydroxy-5H-cyclohepta(b)pyridin-5-one

Product 1

HCID 57911448(R)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-oneYield 73%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

In a 1L round-bottomed flask was (R)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (19.14 g, 108 mmol) (azeotroped with dry benzene) in CH2Cl2 (300 mL) to give a tan solution. After cooling to 0° C., TIPS-OTf (29.3 mL, 108 mmol) and Et3N (30.1 mL, 216 mmol) were added via syringe, and the mixture was stirred at 0° C. for 1h. LCMS indicated complete conversion. Volatiles were stripped off and the residue was partitioned between NaHCO3 solution and EtOAc. The layers were separated and the organic layer was washed with brine, dried and concentrated to a tan oil (37 g). It was purified by FCC up to 20% EtOAc/hexane to afford the product as a white solid (26.3 g, 73% for two steps). MS(ESI)[M+H+]=334.37.

Workup

  1. customto give a tan solution
  2. customthe residue was partitioned between NaHCO3 solution and EtOAc
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated to a tan oil (37 g)
  7. customIt was purified by FCC up to 20% EtOAc/hexane

Sources & evidence

ORD record
ord-9f83e674f13d41f5b8bb4a53e4bb6824
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044043B2

Reaction notes

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