2,6-Lutidine → HCID 67430702, compound

HRID 1660699Notes

Reaction equation

HRID 1660699 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C@H:5]([OH:21])[C@H:6]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH:7]([CH3:9])[CH3:8].N1C(C)=CC=CC=1C.O([Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C@H:5]([O:21][Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[C@H:6]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 11738397HCID 11738397, compound

Product 1

HCID 67430702HCID 67430702, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of the crude alcohol 12 (2.7 g, 9.1 mmol) in CH2Cl2 (10 mL) under argon, cooled to 0° C., 2,6-lutidine (2.6 mL, 22.7 mmol) and triisopropylsilyl triflate (3.6 mL, 13.6 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 2 h and diluted with CH2Cl2 (25 mL). The organic layer was separated and washed with 10% HCl (50 mL), NaHCO3 (50 mL, sat) and NaCl (50 mL, sat), dried (Na2SO4), filtered and concentrated. The crude oil was purified by column chromatography (silica gel, diethyl ether/hexanes 2:98 to 15:85) to yield 13 (2.9 g, 70%) as colorless oil. 1H-NMR (500 MHz, CDCl3): 0.88 (d, J=6.8 Hz, 3H), 0.92 (d, J=6.7 Hz, 3H), 1.01-1.07 (m, 2H), 1.97-2.04 (m, 1H), 2.53 (dd, J=15.3 and 4.7 Hz, 1H), 2.60 (dd, J=15.2 and 7.5 Hz, 1H), 3.57 (s, 3H), 3.59-3.65 (m, 1H), 4.34-4.40 (m, 1H), 4.78 (d, J=10.3 Hz, 1H), 5.06-5.09 (m, 2H), 7.27-7.35 (m, 5H).

Workup

  1. waitat room temperature for 2 h
  2. customThe organic layer was separated
  3. washwashed with 10% HCl (50 mL), NaHCO3 (50 mL, sat) and NaCl (50 mL, sat)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude oil was purified by column chromatography (silica gel, diethyl ether/hexanes 2:98 to 15:85)

Sources & evidence

ORD record
ord-3f34305ea6994773a64a74a1d56666e4
Source dataset
uspto-grants-2011_10
Patent number
US08030279B2

Reaction notes

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