Boron tribromide → (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-ol

HRID 422156Notes

Reaction equation

HRID 422156 reaction equation
C[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)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:24][C@@:7]12[CH2:8][CH2:9][C@@H:10]3[C@:15]([CH3:21])([CH2:14][CH2:13][CH2:12][C:11]3([CH3:23])[CH3:22])[C@H:16]1[CH2:17][S:18][C:19]1[C:6]2=[CH:5][CH:4]=[C:3]([OH:2])[CH:20]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 53240551(1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene

Product 1

HCID 53240553(1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-olYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-triene (51) (0.25 g, 0.73 mmol) in CH2Cl2 (10 mL), cooled to 0° C., a solution of BBr3 (1.0 M in CH2Cl2, 2.90 mL, 2.90 mmol) was added and the resulting mixture was stirred at room temperature for 24 h. The reaction was quenched with MeOH (3×10 mL) and concentrated to dryness. Purification by column chromatography on silica gel (Hexanes/EtOAc, 10:1) gave (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-ol (Compound No. 53) (0.22 g, 92%) as a white solid. 1H NMR (CDCl3): δ 7.14 (d, 1H), 6.49 (m, 2H), 4.45 (br s, 1H), 2.95 (q, 2H), 2.40 (m, 1H), 1.84-1.35 (m, 9H), 1.20 (s, 3H), 1.18-0.98 (m, 2H), 0.95 (s, 3H), 0.88 (m, 3H), 0.85 (s, 3H).

Workup

  1. customThe reaction was quenched with MeOH (3×10 mL)
  2. concentrationconcentrated to dryness
  3. customPurification by column chromatography on silica gel (Hexanes/EtOAc, 10:1)

Sources & evidence

ORD record
ord-9d545bd108ae45258a7796d658dc7dd2
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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