Lithium borohydride → (1S,2R,3R,4S)-3,4-Bis(hydroxymethyl)-2-(2-methylphenyl)cyclohexanol

HRID 1644775노트

반응식

HRID 1644775 반응식
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8](OCC)=[O:9])[C@@H:4]([C:13](OCC)=[O:14])[C@@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].[Li+].[BH4-]>C1COCC1>[OH:14][CH2:13][C@@H:4]1[C@@H:5]([CH2:8][OH:9])[CH2:6][CH2:7][C@H:2]([OH:1])[C@H:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 66774775Diethyl(1S,2S,3R,4S)-3-(2-methylphenyl)-4-hydroxycyclohexane-1,2-dicarboxylate

생성물 1

HCID 66774537(1S,2R,3R,4S)-3,4-Bis(hydroxymethyl)-2-(2-methylphenyl)cyclohexanol수율 90.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

To a solution of diethyl (1S,2S,3R,4S)-4-hydroxy-3-(2-methylphenyl)cyclohexane-1,2-dicarboxylate (Step G, 64.1 g, 192 mmol) in 250 mL THF under nitrogen atmosphere was slowly added LiBH4 powder (16.7 g, 767 mmol, excess) at 0° C. The resulting mixture was heated at 75° C. for 12 hr then cooled to RT. The reaction mixture was carefully quenched by addition of 30 mL water at 0° C., then 30 mL 2 N hydrochloric acid. The organic layer was separated and the aqueous was extracted with EtOAc. The combined organic extracts were washed with aqueous NaHCO3, dried over Na2SO4, filtered and the solvent evaporated under vacuum to give 43.7 g of the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 7.30-7.13 (4H, m), 3.93-3.68 (3H, m), 3.53 (1H, dd, J1=11.2 Hz, J2=2.3 Hz), 3.27 (1H, dd, J1=11.2 Hz, J2=5.1 Hz), 2.85 (1H, t, J=10.5 Hz), 2.39 (3H, s), 2.19 (1H, m), 1.86 (3H, bs), 1.67 (2H, m), 1.55 (1H, m), 1.45 (1H, m).

후처리

  1. customat 0° C
  2. temperaturethen cooled to RT
  3. customThe reaction mixture was carefully quenched by addition of 30 mL water at 0° C.
  4. customThe organic layer was separated
  5. extractionthe aqueous was extracted with EtOAc
  6. washThe combined organic extracts were washed with aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum

출처 및 근거

ORD 기록
ord-14bc70c667fd4cf9bae7b7a2529b5201
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124633B2

반응 노트

불러오는 중…