Dichloromethane → HCID 53248331, compound

HRID 1913953Notes

Reaction equation

HRID 1913953 reaction equation
[Si]([O:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C@@H:23]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24][CH:25]([CH3:27])[CH3:26])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(Cl)Cl>C1COCC1>[OH:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C@@H:23]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 58345823HCID 58345823, compound

Product 1

HCID 53248331HCID 53248331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude (4) (12.0 g, 24.3 mmol) in THF (200 mL) at 0° C. was added TBAF (1.0 M in THF, 1.25 eq, 30.4 mL, 30.4 mmol) and the reaction was warmed to RT and stirred for 2 h. The reaction was quenched with sat. aq. NH4Cl, organic layer washed with brine, dried (MgSO4), filtered and concentrated. The crude residue was purified by chromatography on SiO2 (3:7, EtOAc:hexanes) to yield 5.51 g (88%, 2 steps) as a colorless oil. [α]D −12.7 (c 1.0, CH2Cl2); 1H NMR δ 5.56 (dt, 1H, J=15.3, 6.9 Hz), 5.41 (dd, 1H, J=15.4, 6.4 Hz), 4.41 (bs, 1H), 4.06 (bm, 1H), 3.65 (appbq, 2H, J=5.7 Hz), 2.29 (q, 2H, J=6.3 Hz), 1.76 (bs, 1H), 1.68 (m, 1H), 1.44 (s, 9H), 1.33 (m, 2H), 0.92 (m, 6H); 13C NMR δ 155.4, 134.3, 126.9, 79.2, 61.5, 50.9, 44.5, 35.6, 28.3, 24.6, 22.5; EIMS m/z 257 ([M]+, 10), 227 (55), 171 (65); HRMS (EI) m/z calcd for C14H27NO3 257.1991, found 257.1994.

Workup

  1. customThe reaction was quenched with sat. aq. NH4Cl, organic layer
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by chromatography on SiO2 (3:7, EtOAc:hexanes)
  7. customto yield 5.51 g (88%, 2 steps) as a colorless oil

Sources & evidence

ORD record
ord-02545504028c40f29ffe8cc54326d916
Source dataset
uspto-grants-2013_12
Patent number
US08609850B2

Reaction notes

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