Water → HCID 59627881, compound

HRID 2088401Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][C@@H:11]([CH:13]=[CH2:14])[C@H:10]([O:15][Si](CC)(CC)CC)[C:9]=2[CH3:23])=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>C1COCC1>[CH3:23][C:9]1[C@@H:10]([OH:15])[C@H:11]([CH:13]=[CH2:14])[CH2:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 31b (50 mg, 0.152 mmol) in THF (1 ml) at 0° C. was added tetrabutylammonium fluoride (0.152 ml of 1 M solution in THF, 0.152 mmol) dropwise. The reaction mixture was stirred at 0° C. for 30 min and water (1 ml) and ethyl acetate (2 ml) were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×2 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography on silica (16-50% EtOAc/hexanes) afforded pure alcohol 5b (28 mg, 83%) as a white solid: [α]22D=−26.0 (c=0.3, CHCl3); TLC Rf=0.25 (silica gel, 50% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 8.43 (s, 1H), 7.46 (dd, J=1.8 Hz, 7.8 Hz, 1H), 7.18 (d, J=7.8 Hz, 1H), 6.0-5.95 (m, 1H), 5.14 (d, J=16.8 Hz, 1H), 5.08 (d, J=10.2 Hz, 1H), 4.48 (s, 1H), 2.96-2.91 (m, 1H), 2.69-2.60 (m, 2H), 2.32 (s, 3H), 2.03 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 153.6, 149.9, 140.2, 139.4, 136.7, 135.6, 131.2, 122.3, 115.4, 86.4, 52.3, 38.5, 18.5, 13.2; HRMS calcd for C14H17NO+Na+ 238.1208; found 238.1191 [M+Na+].

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (2×2 ml)
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customPurification by flash column chromatography on silica (16-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e2d9c3ab800048839e1eb9364e2c1b7d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435983B2

Reaction notes

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