Tetrabutylammonium Fluoride → HCID 86638864, compound

HRID 2065817Notes

Reaction equation

HRID 2065817 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH:21]1[CH2:23][CH:22]1[C@@H:24]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:25][CH:26]([CH3:28])[CH3:27])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:18][CH2:19][CH2:20][CH:21]1[CH2:23][CH:22]1[C@@H:24]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:25][CH:26]([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86638861HCID 86638861, compound

Product 1

HCID 86638864HCID 86638864, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the TBDPS-protected alcohol 11b (320 mg, 0.588 mmol) in dry THF (5 mL) at 0° C. was added TBAF (1.0M/THF, 0.74 mL, 0.735 mmol), and the reaction mixture was allowed to warm to rt while stirring under argon for 7 h, then quenched with sat. aq. NH4Cl and diluted with EtOAc. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography (SiO2, 5:5, hexanes/EtOAc) afforded 166 mg (92%) of the title compound as a colorless oil. [α]D23-21.6 (c 1.0, DCM); 1H NMR (300 MHz, CDCl3) δ 7.42-7.28 (m, 5 H), 5.10 (m, 2 H), 4.76 (appbd, 1H, J=5.7 Hz), 3.63 (bs, 2 H), 3.04 (m, 1 H), 2.12-1.98 (bs, 1 H), 1.83-1.62 (m, 2 H), 1.42 (t, 2H, J=7.0 Hz), 1.16-0.95 (m, 2 H), 0.90 (appt, 6H, J=7.0 Hz), 0.53 (sept, 1H, J=4.3 Hz), 0.42 (dt, 1H, J=8.4, 4.5 Hz), 0.34 (dt, 1H, J=8.4, 5.0 Hz); HRMS (ESI) m/z calcd for C18H27NO3Na 328.1889, found 328.1860.

Workup

  1. customquenched with sat. aq. NH4Cl
  2. additiondiluted with EtOAc
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5be3f67c1d242dcb332cc8cf8ff72d9
Source dataset
uspto-grants-2012_10
Patent number
US08288551B2

Reaction notes

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