Water → HCID 69426764, compound

HRID 1295508Notes

Reaction equation

HRID 1295508 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:25])[CH:13]3[CH2:14][CH2:15][CH:9]2[CH2:10][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12]3)[CH:5]=[CH:6][CH:7]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>N1C=CC=CC=1>[OH:25][C:8]1([C:4]2[CH:3]=[C:2]([NH:1][S:27]([CH3:26])(=[O:29])=[O:28])[CH:7]=[CH:6][CH:5]=2)[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH2:12]2

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 69428909HCID 69428909, compound

Product 1

HCID 69426764HCID 69426764, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-(3-Amino-phenyl)-3-(4-methoxy-benzyl)-3-aza-bicyclo[3.2.1]octan-8-ol (2.11 g, 6.23 mmol) in pyridine (15 mL) at 0° C. was charged with methanesulfonylchloride (0.72 mL, 9.35 mmol) dropwise. The reaction was warmed to room temperature and judged complete by TLC after 3 h. Following a water addition (20 mL), the product was extracted with EtOAc (4×30 mL), the organic layer was washed with saturated aqueous NaCl solution (6×50 mL), dried over Na2SO4, filtered and concentrated to give a crude orange liquid. Flash chromatography provided the title compound as a yellow semi-solid (1.28 g, 49%). (TLC 50% EtOAc/Hexanes Rf 0.24); 400 MHz 1H NMR (400 MHz, CDCl3) δ 7.30 (d, J=8.7 Hz, 2H), 7.27 (m, 3H), 7.14 (dd, J=7.1, 2.1 Hz, 1H), 6.83 (d, J=8.7 Hz, 2H), 3.77 (s, 3H), 3.53 (m, 2H), 2.96 (s, 3H), 2.82 (m, 2H), 2.60 (m, 2H), 2.36 (br s, 2H), 1.78 (m, 2H), 1.36 (m, 2H); APCI MS m/z 417.1 (M+1)+; LCMS m/z 417.1 (M+1)+.

Workup

  1. extractionthe product was extracted with EtOAc (4×30 mL)
  2. washthe organic layer was washed with saturated aqueous NaCl solution (6×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude orange liquid

Sources & evidence

ORD record
ord-20efd03835e54c9c88c67d08470ba152
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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