Potassium Carbonate → HCID 10016807, compound

HRID 326413Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:15][C@H:14]2[N:16]([CH3:17])[C@H:11]([CH2:12][CH2:13]2)[C@H:10]1[C:18](OC)=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:15][C@H:14]2[N:16]([CH3:17])[C@H:11]([CH2:12][CH2:13]2)[C@H:10]1[CH2:18][OH:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

The TBDMS-protected compound of Example 1 (900 mg, 2.88 mmol) was dissolved in 12 mL of methylene chloride. The solution was cooled to -78° C., and a 1M solution of diisobutylaluminum hydride in hexanes (11.5 mL, 11.5 mmol) was added. The reaction mixture was stirred at -78° C. for 4 hr. A saturated solution of K2CO3 was added to quench the reaction. The aqueous layer was extracted with chloroform. The combined organic layers were washed with water and brine and dried over MgSO4. The solvent was evaporated in vacuo, and the residue was chromatographed using methanol as eluent to give 650 mg of the title alcohol 3 (79% yield): IR (thin film) 3453, 2947, 2899, 2857, 1472, 1252, 1098, 837 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 4.12-3.85 (m, 3H), 3.45-3.37 (m, 1H), 3.21-3.17 (m, 1H), 2.22 (s, 3H), 2.20-1.50 (m, 8H), 0.88 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3, 75.46 MHz) δ 66.9, 65.7, 63.6, 61.5, 46.5, 41.2, 40.6, 26.0, 25.4, 18.3, 6.6, 6.3; mass spectrum m/z 285 (M+), 228, 154, 126, 83; HRMS (FAB) calcd for C15H32NO2Si (MH+) 286.2194, found 286.2215.

Workup

customto quench
customthe reaction
extractionThe aqueous layer was extracted with chloroform
washThe combined organic layers were washed with water and brine
dry with materialdried over MgSO4
customThe solvent was evaporated in vacuo
customthe residue was chromatographed

Sources & evidence

ORD record: ord-1fd044a16f5d4273a8325ade4b953d37
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05268480

Reaction notes

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