Water → HCID 86595513, compound

HRID 1295511Notes

Reaction equation

HRID 1295511 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:23])[CH:13]3[CH2:14][CH2:15][CH:9]2[CH2:10][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]3)[CH:5]=[CH:6][CH:7]=1.[CH3:24][O:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29].O>N1C=CC=CC=1>[CH2:16]([N:11]1[CH2:10][CH:9]2[C:8]([C:4]3[CH:3]=[C:2]([NH:1][S:28]([CH2:27][CH2:26][O:25][CH3:24])(=[O:30])=[O:29])[CH:7]=[CH:6][CH:5]=3)([OH:23])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 134802212-Methoxyethane-1-sulfonyl chlorideHCID 694262238-(3-Amino-phenyl)-3-benzyl-3-aza-bicyclo[3.2.1]octan-8-ol

Product 1

HCID 86595513HCID 86595513, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-(3-Amino-phenyl)-3-benzyl-3-aza-bicyclo[3.2.1]octan-8-ol (1.63 g, 5.28 mmol) stirred in pyridine (20 ml) at 0° C. was charged with 2-methoxy-ethanesulfonyl chloride (1.26 g, 7.93 mmol) dropwise causing a color change from yellow to bright orange. The reaction was warmed to room temperature and judged complete by TLC after 1 h. Following addition of water (20 ml), the product was extracted with EtOAc (4×30 ml), washed with saturated aqueous NaCl solution (6×30 ml), dried over Na2SO4, filtered and concentrated to a crude red oil (2.37 g, >100%). 1H NMR (400 MHz, CDCl3) δ 7.35–7.10 (m, 4H), 3.78 (ddd, J=7.5, 3.3, 2.1 Hz, 2H), 3.59 (s, 2H), 3.36 (d, J=2.5 Hz, 3H), 3.17, (m, 2H), 2.85 (d, J=16.3 Hz, 3H), 2.61 (d, J=8.3 Hz, 2H), 2.36 (s, 2H), 1.79 (d, J=7.0 Hz, 2H), 1.37 (d, J=10.0 Hz, 2H); APCI MS m/z 431.2 (M+1)+.

Workup

  1. extractionthe product was extracted with EtOAc (4×30 ml)
  2. washwashed with saturated aqueous NaCl solution (6×30 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a crude red oil (2.37 g, >100%)

Sources & evidence

ORD record
ord-11b8179da083468aaba329e59a4955aa
Source dataset
uspto-grants-2007_07
Patent number
US07241887B2

Reaction notes

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