Boron tribromide → (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4,6-diol

HRID 422147노트

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HRID 422147 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:18](=[C:19]([O:21]C)[CH:20]=1)[O:17][CH2:16][C@H:15]1[C@@:6]2([CH3:26])[CH2:7][CH2:8][C@@H:9]2[C@:14]1([CH3:23])[CH2:13][CH2:12][CH2:11][C:10]2([CH3:25])[CH3:24].B(Br)(Br)Br>C(Cl)Cl>[CH3:26][C@@:6]12[CH2:7][CH2:8][C@@H:9]3[C@:14]([CH3:23])([CH2:13][CH2:12][CH2:11][C:10]3([CH3:24])[CH3:25])[C@H:15]1[CH2:16][O:17][C:18]1[C:5]2=[CH:4][C:3]([OH:2])=[CH:20][C:19]=1[OH:21]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 53240452(1R,10R,11S,16S)-4,6-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene

생성물 1

HCID 53240454(1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4,6-diol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1R,10R,11S,16S)-4,6-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 42) (0.69 g, 1.9 mmol) in CH2Cl2 (20 mL), cooled to 0° C., and a BBr3 solution (7.3 mL, 1 M in CH2Cl2, 7.3 mmol) was added dropwise. The ice bath was removed and the reaction was stirred at room temperature for 6 h. The reaction was quenched with MeOH (20 mL) and concentrated. The quenching and concentration steps were repeated six times. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4,6-diol (Compound No. 43) (0.42 g, 66%) as a pale pink solid. 1H NMR (CDCl3): δ 6.28 (d, 1H), 6.17 (d, 1H), 5.48 (br s, 1H), 4.40 (m, 1H), 4.25 (br s, 1H), 4.15 (t, 1H), 2.20 (m, 1H), 1.80-1.35 (m, 7H), 1.28 (s, 3H), 1.25-1.00 (m, 4H), 0.92 (s, 3H), 0.88 (s, 3H), 0.82 (s, 3H). MS m/z 331 (C21H30O3+H+).

후처리

  1. customThe ice bath was removed
  2. customThe reaction was quenched with MeOH (20 mL)
  3. concentrationconcentrated
  4. concentrationThe quenching and concentration steps
  5. customPurification by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

출처 및 근거

ORD 기록
ord-c0077aaa574844df8631cba9d402772a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101605B2

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