Methanesulfonyl chloride → HCID 558152, compound

HRID 1086264Notes

Reaction equation

HRID 1086264 reaction equation
C1(CO[CH:9]2[CH:14](OCC3C=CC=CC=3)[CH:13](OCC3C=CC=CC=3)[CH:12](COCC3C=CC=CC=3)[NH:11][CH:10]2[CH:40]([OH:45])[CH2:41][CH2:42][CH2:43]O)C=CC=CC=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[CH:40]1([OH:45])[CH:10]2[N:11]([CH2:12][CH2:13][CH2:14][CH2:9]2)[CH2:43][CH2:42][CH2:41]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54330377HCID 54330377, compound

Product 1

HCID 558152HCID 558152, compoundYield 232.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Compound (XIX) (0.22 g, 0.36 mmoles) in pyridine (15 mL), cooled at -10° C., methanesulfonyl chloride (0.03 mL, 0.39 mmoles) was added. After 6 days, the mixture was evaporated under reduced pressure. The resulting oil was treated with water (5 mL) and saturated aqueous sodium bicarbonate solution (20 mL), then extracted with ether (2×30 mL). The combined organic solution was dried over magnesium sulfate and the solvent evaporated under reduced pressure. Trituration of the resulting oil with ether yielded [1S-(1α,6β,7α,8β,9α,9aβ)]-octahydro-7,8,9-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-2H-quinolizin-1-ol (XX) as white crystals (0.13 g, 60.8%) m.p. 103°-5° C.; IR (KBr) no absorbance 1650-1770 cm-1;MS (CI13 CH4) 594 (MH+), 486 (MH+ --PhCH2OH); 1H nmr (CDCl3) δ 1.2 (m, 1H), 1.4-1.6 (m, 3H), 1.8-2.0 (m, 2H), 2.6-2.8 (t, 1H), 3.0-3.1 (d, 1H), 3.2-3.3 (m, 1H), 3.5-3.9 (m, 4H), 4.2-5.0 (m, 9H), 7.1-7.4 (m, 20H).

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. additionThe resulting oil was treated with water (5 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
  3. extractionextracted with ether (2×30 mL)
  4. dry with materialThe combined organic solution was dried over magnesium sulfate
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-26bc17e3e4b0474da453d7b6fb4129d6
Source dataset
uspto-grants-1991_07
Patent number
US05028614

Reaction notes

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