Sodium Bicarbonate → HCID 10783530, compound

HRID 2256869Notes

Reaction equation

HRID 2256869 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C@:10]1([CH3:31])[C@H:15]2[C@H:16]3[C@H:25]([CH2:26][CH2:27][C@:13]2([CH3:14])[C:12](=[O:30])[CH2:11]1)[C:24]1[CH:23]=[CH:22][C:21]([O:28][CH3:29])=[CH:20][C:19]=1[CH2:18][CH2:17]3)([CH3:9])[CH3:8].C(=O)([O-])O.[Na+]>O1CCCC1>[CH:7]([C@:10]1([CH3:31])[C@H:15]2[C@H:16]3[C@H:25]([CH2:26][CH2:27][C@:13]2([CH3:14])[C@@H:12]([OH:30])[CH2:11]1)[C:24]1[CH:23]=[CH:22][C:21]([O:28][CH3:29])=[CH:20][C:19]=1[CH2:18][CH2:17]3)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10783379HCID 10783379, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10783530HCID 10783530, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (35 mg; 0.92 mmol) was added to a solution of the 15α-isopropyl-15β-methyl ketone (11) (63 mg; 0.19 mmol) in dry tetrahydrofuran (4 ml) at 0° C. After 10 min. at this temperature, saturated aqueous sodium hydrogen carbonate was added. The mixture was filtered, and the clear solution was given the standard work-up (ethyl acetate) to give 15α-isopropyl-3-methoxy-15β-methylestra-1,3,5(10)-trien-17β-ol (15) (60 mg; 95%), [α]D +54° (c 1.3); υmax 3604 cm-1 (OH); δH (200 MHz), 0.88 and 0.92 (each 3H, d, J 6.8 Hz, 15α-CHMe2), 0.96 (3H, s, 13β-Me), 1.13 (3H, s, 15β-Me), 1.73 (1H, dd, J 13.4 and 10.2 Hz, 16-H), 2.13 (1H, dd, J 13.4 and 7.9 Hz, 16-H), 3.54 (1H, dd, J 10.2 and 7.9 Hz, 17α-H), 3.78 (3H, s, 3-OMe), 6.64 (1H, dd, J 2.7 Hz, 4 -H), 6.71 (1H, dd, J 8.5 and 2.7 Hz, 2 -H), and 7.22 (1H, d, J 8.5 Hz, 1-H); δC 14.1 (C-18), 18.2 and 18.6 (15α-CHMe2), 23.6 (C-11), 26.2 (C-7), 28.5 (15β-Me), 29.9 (C-8), 36.6 (C-12), 37.3 (15α-CHMe2), 39.3 (C-6), 40.7 (C-15), 42.7 (C-13), 44.7 (C-9), 45.0 (C-16), 51.8 (C-14), 55.2 (3-OMe), 80.8 (C-17), 111.4 (C-2), 113.6 (C-4), 126.3 (C-1), 133.0 (C-10), 137.6 (C-5), and 157.7 (C-3) (Found: C, 80.4; H, 9.9%; M+, 342. C22H34O2 requires C, 80.65; H, 10.0%; M, 342) .

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-4de544eb9ccc4155b54a7d9b20d86766
Source dataset
uspto-grants-1997_08
Patent number
US05656622

Reaction notes

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