Triethylamine → Methanesulfonic acid 9-(4-methanesulfonyloxy-phenyl)-2-(3-methanesulfonyloxy-propyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-yl ester

HRID 418941Notes

Reaction equation

HRID 418941 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:21][C:20]3[CH:19]=[C:18]([CH2:22][CH2:23][CH2:24][OH:25])[C:17]([OH:26])=[CH:16][C:15]=3[CH:14]3[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]3)=[CH:4][CH:3]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.CNC1C=CC=C(NC)N=1>O.C(OCC)(=O)C.C(Cl)Cl>[CH3:27][S:28]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:21][C:20]3[CH:19]=[C:18]([CH2:22][CH2:23][CH2:24][O:25][S:28]([CH3:27])(=[O:30])=[O:29])[C:17]([O:26][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:16][C:15]=3[CH:14]3[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]3)=[CH:6][CH:7]=1)(=[O:30])=[O:29]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111943672-N,6-N-dimethylpyridine-2,6-diamineHCID 666526959-(4-Hydroxy-phenyl)-2-(3-hydroxy-propyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol

Product 1

HCID 86645827Methanesulfonic acid 9-(4-methanesulfonyloxy-phenyl)-2-(3-methanesulfonyloxy-propyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-yl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 9-(4-Hydroxy-phenyl)-2-(3-hydroxy-propyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol (0.1 g, 0.284 mmol), methanesulfonyl chloride (0.11 g, 0.94 mmol), triethylamine (0.19 g, 1.9 mmol), 2,6-dimethylaminopyridine (0.02 g, cat.) and methylene chloride (5 ml) and stir 15 hours. Remove solvent in vacuo and add ethyl acetate and water. Wash 1× with sodium bicarbonate solution solution followed by water. Dry over anhydrous sodium sulfate and remove solvent in vacuo to yield preparation 133 (0.16 g, g, 96%). 1H NMR (CDCl3): 7.34 (d, J=8.8 Hz, 2H), 7.28 (d, J=8 Hz, 2H), 7.26 (s, 1H), 7.09 (s, 1H), 4.28 (t, J=7.1 and 6.2 Hz, 2H), 3.24 (m, 6H), 3.16 (s, 3H), 3.03 (s, 3H), 2.9 (d, J=11.9 Hz, 1H), 2.82 (t, J=7.5 and 8.4 Hz, 3H), 2.45 (d, J=13.7 Hz, 1H), 2.1 (m, 3H), 1.8-1.0 (m, 6H).

Workup

  1. washWash 1× with sodium bicarbonate solution solution
  2. dry with materialDry over anhydrous sodium sulfate
  3. customremove solvent in vacuo
  4. customto yield
  5. custompreparation 133 (0.16 g, g, 96%)

Sources & evidence

ORD record
ord-8efaac1e28184cce94b75122ecea6234
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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