2,6-Lutidine → HCID 68519870, compound

HRID 1948368Notes

Reaction equation

HRID 1948368 reaction equation
[Br:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13].FC(S(O[Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])(=O)=O)(F)F.N1C(C)=CC=CC=1C>C(Cl)Cl>[Br:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[O:13][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 12414165HCID 12414165, compound

Product 1

HCID 68519870HCID 68519870, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 4-bromo-3-hydroxypiperidine-1-carboxylate (Preparation: Izamanishi, T. et al; 1982, Chem. Pharm. Bull., 30: 3617-3623) (10.17 g) was dissolved in anhydrous DCM (100 mL) under an argon atmosphere and cooled to 0° C. tert-Butyldimethylsilyl trifluoromethylsulfonate (10.2 mL) was added dropwise via syringe, followed by 2,6-lutidine (4.7 mL), also added dropwise via syringe. The reaction was stirred overnight, slowly warming to room temperature, then diluted with DCM (200 mL) and washed with saturated aqueous NaHCO3 (150 mL), saturated aqueous NH4Cl ((150 mL), brine (100 mL), dried over anhydrous MgSO4 and concentrated in vacuo, yielding the title compound as a crude product (15.1 g, 102%). MS (GC-EI)[(M-C4H7)+]: 310, 312 for C14H28BrNO3Si; NMR (CDCl3): 0.10 (s, 3H), 0.12 (s, 3H), 0.88 (s, 9H), 1.24 (t, 3H), 1.87 (m, 1H), 2.34 (m, 1H), 2.84-3.40 (m, 2H), 3.69 (m, 2H), 3.93 (m, 2H), 4.13 (q, 2H).

Workup

  1. additionwas added dropwise via syringe
  2. additionalso added dropwise via syringe
  3. washwashed with saturated aqueous NaHCO3 (150 mL), saturated aqueous NH4Cl ((150 mL), brine (100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-620565e5fc414582a4c3013de0e93679
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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