Methanol → HCID 25133549, compound

HRID 1889122Notes

Reaction equation

C[O:2][C:3](=O)[C@@H:4]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][CH2:6][C:7](OC)=[O:8].[BH4-].[Li+].CO>CCOCC.Cl>[Si:12]([O:11][C@@H:4]([CH2:5][CH2:6][CH2:7][OH:8])[CH2:3][OH:2])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 5 (0.8 g, 1.8 mmol) was dissolved in dry Et2O (8.5 mL) and the solution was cooled to 0° C., afterward lithium borohydride (0.12 g, 5.4 mmol) and dry methanol (0.22 mL, 5.4 mmol) were sequentially added. The resulting suspension was stirred at 23° C. for 24 h, then a few drops of 6 N HCl were added and the salts were filtered off. The filtrate was concentrated under reduced pressure and the residue was purified by flash-chromatography (1:1 EtOAc/Hex) to furnish 0.61 g (93%) of 6a as a colourless oil: [α]D20=−15.6 (c 3.1, CHCl3); 1H NMR (CDCl3) δ 7.70-7.65 (m, 4H), 7.44-7.32 (m, 6H), 3.82-3.77 (m, 1H), 3.53-3.48 (m, 2H), 3.45-3.41 (m, 2H), 1.65-1.47 (m, 4H), 1.05 (s, 9H); 13C NMR (CDCl3) δ 135.9, 135.7, 133.8, 133.7, 130.1, 129.8, 127.7, 127.6, 73.6, 65.7, 62.7, 29.7, 28.0, 27.0, 19.3.

Workup

filtrationthe salts were filtered off
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by flash-chromatography (1:1 EtOAc/Hex)

Sources & evidence

ORD record: ord-d52f3d6570a7433988f52af77c3ad1fa
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501961B2

Reaction notes

Loading…