Acetic Anhydride → (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-yl acetate

HRID 1879363Notes

Reaction equation

HRID 1879363 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:19][CH2:18][C@@H:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C@H:10]1[OH:31].[C:32](OC(=O)C)(=[O:34])[CH3:33].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:32]([O:31][C@@H:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[C@H:17]([O:20][Si:21]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:22]([CH3:23])[CH3:24])[CH2:18][CH2:19][C@H:9]1[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 57911423(5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol

Product 1

HCID 67116262(5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-yl acetateYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottom flask was dissolved (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol (1.004 g, 2.243 mmol) in methylene chloride (20 mL) to give a colorless solution. Acetic anhydride (0.423 mL, 4.49 mmol) and triethylamine (0.938 mL, 6.73 mmol) were added, followed by DMAP (0.055 g, 0.449 mmol). The mixture was stirred at room temperature under nitrogen. 2 h: LCMS showed complete conversion. It was quenched with Sodium bicarbonate solution and diluted with ethyl acetate. The layers were separated. The organic layer was washed with brine, dried and concentrated to give a colorless oil (100%), which was directly carried onto next reaction without further purification and characterization. MS(ESI)[M+H+]=490.26.

Workup

  1. customto give a colorless solution
  2. custom2 h
  3. customIt was quenched with Sodium bicarbonate solution
  4. additiondiluted with ethyl acetate
  5. customThe layers were separated
  6. washThe organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e5dc486976554bac9e12ebd308174cf0
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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