Water → HCID 18652192, compound

HRID 1587035Notes

Reaction equation

HRID 1587035 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:7]([CH2:8][CH2:9][C:10]3[C@@H:23]2[CH2:22][C@H:21]([O:28][C:29](=[O:35])[C:30]([CH3:34])([CH3:33])[CH2:31][CH3:32])[C@@:20]2([CH3:36])[C:11]=3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:19])[CH2:16][CH:17]=[CH2:18])[CH2:6]1)(=[O:3])[CH3:2].C(O)(C)(C)C.[OH2:42].[OH2:43].C[N+]1([O-])CCOCC1>C(OCC)(=O)C.CCOCC.[Os](=O)(=O)(=O)=O>[C:1]([O:4][C@@H:5]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:7]([CH2:8][CH2:9][C:10]3[C@@H:23]2[CH2:22][C@H:21]([O:28][C:29](=[O:35])[C:30]([CH3:34])([CH3:33])[CH2:31][CH3:32])[C@@:20]2([CH3:36])[C:11]=3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:19])[CH2:16][CH:17]([OH:43])[CH2:18][OH:42])[CH2:6]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 67857040HCID 67857040, compound

Product 1

HCID 18652192HCID 18652192, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3α-acetoxy-12α-(2,2-dimethyl)butyryloxy-5β-chola-8(14),23-diene (2.5 g), osmium tetroxide (0.092 g), tert-butyl alcohol (8 ml), and water (2.3 ml) is added 4-methylmorpholine-N-oxide hydrate (0.334 g). The mixture is stirred for about 2 hours at room temperature, diluted with 20% ethyl acetate in ether and washed with aqueous sodium bisulfite. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product which is used, without further treatment, for the next step.

Workup

  1. washwashed with aqueous sodium bisulfite
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-130da88bfc2a425db88a40b5dceb2788
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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