Tetrabutylammonium Fluoride → HCID 67271139, compound

HRID 601712Notes

Reaction equation

HRID 601712 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([O:21][Si](C(C)C)(C(C)C)C(C)C)[CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2[CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:9][C:8](=[O:45])[NH:7]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:49][C:47]1[CH:46]=[C:4]([CH:3]=[C:2]([F:1])[CH:48]=1)[CH2:5][C@H:6]1[C@@H:10]([C@H:11]2[CH2:20][C:19]3[C:14](=[C:15]([OH:21])[CH:16]=[CH:17][CH:18]=3)[CH2:13][N:12]2[CH:32]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:9][C:8](=[O:45])[NH:7]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67270604HCID 67270604, compound

Product 1

HCID 67271139HCID 67271139, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-benzhydryl-8-(triisopropylsilyloxy)-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step F (13), 200 mg, 0.3 mmol) in THF (5 mL) was added tetrabutylammonium fluoride (118 mg, 0.45 mmol). The mixture was stirred at rt for 1 h. Solvent was removed and the crude mixture was purified by silica gel Flash Chromatography to give 95 mg of the title compound (60% yield): 1H NMR (CD3OD, 500 MHz) δ 2.51-2.56 (1H, m), 2.68 (1H, d, J=20 Hz), 3.22 (1H, dd, J=5, 20 Hz), 3.35 (1H, m), 3.53 (1H, dd, J=5, 15 Hz), 3.80 (1H, d, J=15 Hz), 4.06-4.12 (1H, m), 4.21 (1H, m), 4.80-4.83 (1H, m), 4.91 (1H, s), 6.57 (1H, d, J=10 Hz), 6.66 (1H, d, J=5 Hz), 6.84-6.88 (3H, m), 6.98-7.01 (1H, m), 7.22 (2H, dd, J=10, Hz), 7.28-7.34 (4H, m), 7.46-7.50 (4H, m). MS (ESI) (M−H)− 525.17.

Workup

  1. customSolvent was removed
  2. customthe crude mixture was purified by silica gel Flash Chromatography

Sources & evidence

ORD record
ord-0612684879f24712b86220b207bc35fd
Source dataset
uspto-grants-2011_03
Patent number
US07902218B2

Reaction notes

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