Hydrochloric Acid → HCID 69427878, compound

HRID 1295503Notes

Reaction equation

HRID 1295503 reaction equation
[CH:1]12[CH:8]([C:9]3[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.Cl.C([O-])([O-])=O.[Na+].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>[OH-].[Na+].C(Cl)Cl>[CH2:27]([O:26][C:24]([N:3]1[CH2:4][CH:5]2[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=3)[CH:1]([CH2:7][CH2:6]2)[CH2:2]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 58907750HCID 58907750, compound

Product 1

HCID 69427878HCID 69427878, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-(3-Aza-bicyclo[3.2.1]oct-8-yl)-phenol as HCl salt (547 mg, 1.93 mmol) was stirred vigorously in 1N NaOH (10 mL), saturated aqueous Na2CO3 solution (20 mL) and CH2Cl2 (30 mL) then charged with benzyl chloroformate (5 mL, 35.0 mmol) slowly via syringe. After stirring overnight, the layers were separated and the product was extracted with CH2Cl2 (1×10 mL), washed with saturated aqueous NaHCO3 solution, dried through a cotton plug and concentrated to a brown liquid. Flash chromatography provided the desired product as a thick clear oil (420 mg, 65%). (TLC 30% EtOAc/hexanes Rf 0.34); 1H NMR (400 MHz, CDCl3) δ 7.33 (m, 5H), 7.11 (t, J=7.9 Hz, 1H), 6.73 (d, J=7.9 Hz, 1H), 6.71 (s, 1H), 6.66 (d, J=7.9 Hz, 1H), 5.14 (s, 2H), 4.05 (dd, J=12.2 Hz, 2.7 Hz, 1H), 3.96 (dd, J=12.2, 2.7 Hz, 1H), 3.09 (m, 2H), 2.85 (s, 1H), 2.50 (br s, 1H), 2.46 (br s, 1H), 1.64 (m, 2H), 1.48 (m, 2H).

Workup

  1. customthe layers were separated
  2. extractionthe product was extracted with CH2Cl2 (1×10 mL)
  3. washwashed with saturated aqueous NaHCO3 solution
  4. customdried through a cotton plug
  5. concentrationconcentrated to a brown liquid

Sources & evidence

ORD record
ord-a13b85da77304b55b83adc110b25b56f
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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