Pyridine → (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate

HRID 422140Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[C:19]2[C:6]([C@@:7]3([CH3:24])[C@H:16]([CH2:17][S:18]2)[C@:15]2([CH3:21])[C@H:10]([C:11]([CH3:23])([CH3:22])[CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8]3)=[C:5]([OH:25])[CH:4]=1.N1C=CC=CC=1.[O:32](S(C(F)(F)F)(=O)=O)[S:33]([C:36]([F:39])([F:38])[F:37])(=O)=[O:34]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[S:33]([O:25][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[C:19]2[C:6]=1[C@@:7]1([CH3:24])[C@H:16]([CH2:17][S:18]2)[C@:15]2([CH3:21])[C@H:10]([C:11]([CH3:23])([CH3:22])[CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8]1)(=[O:34])=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol (Compound No. 29) (0.61 g, 1.69 mmol) in CH2Cl2 (40 mL), pyridine (0.20 g, 2.54 mmol) was added and the mixture was cooled to 0° C. Tf2O (0.62 g, 2.20 mmol) was added dropwise to the reaction mixture and stirred for 1.5 h. The reaction was diluted with CH2Cl2 and washed with water (2×40 mL). The organic layer was separated, dried (Na2SO4) and concentrated giving (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate (Compound No. 32) (0.825 g, 98%) as a yellow foam. 1H NMR (CDCl3): δ 6.58 (d, 2H), 3.75 (s, 3H), 2.90 (m, 3H), 1.80-1.40 (m, 8H), 1.38 (s, 3H), 1.25-1.00 (m, 2H), 0.95 (s, 3H), 0.90 (m, 1H), 0.85 (s, 3H), 0.80 (s, 3H).

Workup

washwashed with water (2×40 mL)
customThe organic layer was separated
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-1cc7719550f247a58bf1f5f2909b3b4b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101605B2

Reaction notes

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