Hydrochloric Acid → HCID 11436260, compound

HRID 2378510Notes

Reaction equation

HRID 2378510 reaction equation
C(OC(O[C:7]12[CH2:21][CH:20]([CH3:22])[CH2:19][C:18](=[O:23])[CH:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)C)C.[CH3:24][CH:25]1[CH2:39][C:38]2([O:40][Si](C)(C)C)[CH:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[C:27](=[O:45])[CH2:26]1.C(OC([O:53][C:54]12[CH2:68][CH:67]([CH3:69])[CH2:66][C:65](=[O:70])[CH:64]1[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]2)C)CCC.Cl>O>[CH3:22][CH:20]1[CH2:21][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]=2[C:18](=[O:23])[CH2:19]1.[OH:40][C@:38]12[CH2:39][C@@H:25]([CH3:24])[CH2:26][C:27](=[O:45])[C@H:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2.[OH:53][C@@:54]12[CH2:68][C@H:67]([CH3:69])[CH2:66][C:65](=[O:70])[C@@H:64]1[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 68822387HCID 68822387, compoundHCID 68822771HCID 68822771, compoundHCID 68847088HCID 68847088, compound

Product 3

HCID 11436260HCID 11436260, compoundHCID 15986744HCID 15986744, compoundHCID 45380105HCID 45380105, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

When the reaction was done with (18), (19) or (27), the reaction mixture, obtained above after a conversion of about 40%, can be alternatively treated 10 minutes with a mixture of 0.4 ml H2O and 0.4 ml of an aqueous 1N HCl solution. After extraction of the aqueous layer with diethyl ether the organic layer was washed (saturated aqueous NaHCO3 solution, H2O), dried over MgSO4 and filtered. The solvent was removed under vacuum and the residue was purified by flash chromatography to yield in the desired product, i.e. (1R,11S,14R)-1-hydroxy-14-methyl-bicyclo[9.4.0]pentadecan-12-one or (1S,11R,14S)-1-hydroxy-14-methyl-bicyclo[9.4.0]pentadecan-12-one or an optically active mixture of said stereoisomers depending on the configuration of the alkoxide and (S)-14-methyl-bicyclo[9.4.0]pentadec-1(11)-en-12-one or (R)-14-methyl-bicyclo[9.4.0]pentadec-1(11)-en-12-one or an optically active mixture of said stereoisomers depending on the configuration of the alkoxide.

Workup

  1. customthe reaction mixture, obtained above after a conversion of about 40%
  2. extractionAfter extraction of the aqueous layer with diethyl ether the organic layer
  3. washwas washed (saturated aqueous NaHCO3 solution, H2O)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b4d35eade66b46828946c7acc0c1b3ed
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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