Potassium Carbonate → HCID 66910196, compound

HRID 910603Notes

Reaction equation

HRID 910603 reaction equation
[CH3:1][Si:2]([CH3:39])([C:35]([CH3:38])([CH3:37])[CH3:36])[O:3][C@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[CH:6]([C@@H:7]([O:31]C(=O)C)[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[O:23][Si:24]([CH3:30])([CH3:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:5]1.[CH3:40][Si:41]([CH3:78])([C:74]([CH3:77])([CH3:76])[CH3:75])[O:42][C@@H:43]1[CH2:60][CH2:59][C@@:58]2([CH3:61])[CH:45]([C@@H:46]([O:70]C(=O)C)[CH2:47][C@@H:48]3[C@@H:57]2[CH2:56][CH2:55][C@@:53]2([CH3:54])[C@H:49]3[CH2:50][CH2:51][C@@H:52]2[O:62][Si:63]([CH3:69])([CH3:68])[C:64]([CH3:67])([CH3:66])[CH3:65])[CH2:44]1.C([O-])([O-])=O.[K+].[K+]>CO.O1CCOCC1>[CH3:39][Si:2]([CH3:1])([C:35]([CH3:38])([CH3:37])[CH3:36])[O:3][C@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[CH:6]([C@@H:7]([OH:31])[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[O:23][Si:24]([CH3:29])([CH3:30])[C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:5]1.[CH3:78][Si:41]([CH3:40])([C:74]([CH3:77])([CH3:76])[CH3:75])[O:42][C@@H:43]1[CH2:60][CH2:59][C@@:58]2([CH3:61])[CH:45]([C@@H:46]([OH:70])[CH2:47][C@@H:48]3[C@@H:57]2[CH2:56][CH2:55][C@@:53]2([CH3:54])[C@H:49]3[CH2:50][CH2:51][C@@H:52]2[O:62][Si:63]([CH3:68])([CH3:69])[C:64]([CH3:65])([CH3:66])[CH3:67])[CH2:44]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66910086HCID 66910086, compoundHCID 66910172HCID 66910172, compound

Product 2

HCID 66910183HCID 66910183, compoundHCID 66910196HCID 66910196, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 3β,17β-di(dimethyltert-butylsilyloxy)-6α-acetoxyandrostane and 3α,17β-di(dimethyltert-butylsilyloxy)-6α-acetoxyandrostane (90/10 mixture, 7.58 g) in MeOH/dioxane 1/4 (100 mL), K2CO3 (896 mg) was added. After stirring for 72 h at 40° C., the mixture was quenched by addition of H2O. The organic solvents were evaporated and the concentrated solution was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness to give 3β,17β-di(dimethyltert-butylsilyloxy)androstane-6α-ol and 3α,17β-di(dimethyltert-butylsilyloxy)androstane-6α-ol (90/10 mixture, 6.30 g, 85%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.30 (bb, 1H), 3.55 (bb, 1H), 3.47 (m, 1H), 2.05 (bb, 1H), 1.92-1.73 (m, 2H), 1.68-0.87 (m, 17H), 0.84 (s, 18H), 0.72 (s, 3H), 0.62 (s, 3H), 0.56 (m, 1H), 0.02 (s, 3H), 0.01 (s, 6H), 0.01 (s, 3H).

Workup

  1. customthe mixture was quenched by addition of H2O
  2. customThe organic solvents were evaporated
  3. extractionthe concentrated solution was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b4d36cf94dff4252a1b4d7d556bd3eb2
Source dataset
uspto-grants-2011_09
Patent number
US08022203B2

Reaction notes

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