Tetrahydrofuran → 1289024-48-1

HRID 1879384Notes

Reaction equation

HRID 1879384 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](C(C)C)(C(C)C)C(C)C)[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C@H:10]1[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].O1CCCC1.C(=O)(O)[O-].[Na+]>>[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]([OH:20])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C@H:10]1[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 671162731289024-45-8

Product 1

HCID 584679881289024-48-1Yield 87%

Procedure

To a solution of tert-butyl (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (600 mg, 1.097 mmol) in tetrahydrofuran (15 mL) N-butyl-N,N-dipropylbutan-1-aminium fluoride (1.207 mL, 1.2067 mmol) was added at room temperature. After 1 h, LCMS showed the reaction was complete. Aqueous sodium bicarbonate solution was added (5 ml). The solvent was removed in vacuo and the mixture was extracted with ethyl acetate, dried over sodium sulfate, and concentrated to give a colorless solid which was purified with flash column chromatography to give the desired product (371 mg, 87%): MS(ESI)[M+H+]=547.4.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a colorless solid which
  6. customwas purified with flash column chromatography

Sources & evidence

ORD record
ord-f41365550f69437e9a02dbb3d177f1b4
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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