N-methyl-2-pyrrolidone → (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol

HRID 422144Notes

Reaction equation

HRID 422144 reaction equation
C[O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:26])[C@H:14]([CH2:15][O:16]2)[C@:13]2([CH3:23])[C@H:8]([C:9]([CH3:25])([CH3:24])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.CN1C(=O)CCC1>CCOC(C)=O>[CH3:22][O:21][C:19]1[CH:18]=[C:17]2[C:4]([C@@:5]3([CH3:26])[C@H:14]([CH2:15][O:16]2)[C@:13]2([CH3:23])[C@H:8]([C:9]([CH3:25])([CH3:24])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]3)=[C:3]([OH:2])[CH:20]=1

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 53241986HCID 53241986, compound

Product 1

HCID 53240451(1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-olYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

In a microwave tube, (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 38) (0.15 g, 0.42 mmol), Na2S (0.20 g, 2.6 mmol) and NMP (3 mL) were placed. The tube was sealed and subjected to microwave heating at 180° C. for 1 h. The reaction was cooled to room temperature, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol (Compound No. 39) (0.06 g, 43%) as a colourless solid. 1H NMR (CDCl3): δ 6.15 (d, 1H), 6.00 (d, 1H), 4.93 (s, 1H), 4.27 (m, 1H), 3.97 (t, 1H), 3.68 (s, 3H), 3.00 (m, 1H), 1.75-1.40 (m, 8H), 1.37 (s, 3H), 1.20-0.93 (m, 2H), 0.92 (s, 3H), 0.90 (m, 1H) 0.68 (s, 3H), 0.62 (s, 3H). MS m/z 345 (C22H32O3+H+).

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-629b24c20fed4260b0228be30b6c93bb
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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