Water → 13-Methyl-16-(3,4,5-trimethoxy-benzylidene)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

HRID 1675923

반응식

HRID 1675923 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]3[CH:14]([CH2:15][CH2:16][C:17]=2[CH:18]=1)[CH:13]1[C:9]([CH3:33])([C:10](=[O:32])[C:11](=[CH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)[CH2:12]1)[CH2:8][CH2:7]3.[BH4-].[Na+].C(OCC)(=O)C.O>C1COCC1.CO>[CH3:33][C:9]12[CH2:8][CH2:7][CH:6]3[CH:14]([CH2:15][CH2:16][C:17]4[CH:18]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=43)[CH:13]1[CH2:12][C:11](=[CH:19][C:20]1[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=1)[CH:10]2[OH:32]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 50130353-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

생성물 1

HCID 6734972913-Methyl-16-(3,4,5-trimethoxy-benzylidene)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A solution of 3-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (448 mg, 1.0 mmol, CAB01124) in THF/methanol (1:1, 40 ml) was cooled to 0° C. (ice bath) and sodium borohydride (100 mg, 2.64 mmol) was added. The reaction mixture was stirred for 2 h at this temperature, while it was turning from slightly yellow to colourless. The solution was transferred into a separation funnel and ethyl acetate (100 ml) and water (100 ml) were added. The organic layer was separated, washed with water (50 ml) and brine (50 ml), dried over sodium sulphate and concentrated under reduced pressure. Yield 445 mg (99%) white solid. 1H-NMR (CDCl3, 400 MHz), δ: 0.74 (s, 3H), 1.20-1.60 (m, 6H), 1.90-1.98 (m, 1H), 2.01-2.08 (m, 1H), 2.21-2.41 (m, 3H), 2.74-2.90 (m, 3H), 3.86 (s, 3H), 3.89 (s, 6H), 4.15 (d, J=9.4 Hz, 1H, H-17), 4.62 (s, 1H, —OH), 6.49-6.51 (m, 1H), 6.59 (d, J=2.3 Hz, 1H), 6.63-6.68 (m, 3H), 7.18 (d, J=8.2 Hz, 1H). LRMS (FAB+): 451.3 (100, [M+H]+).

후처리

  1. additionwas added
  2. customThe solution was transferred into a separation funnel
  3. customThe organic layer was separated
  4. washwashed with water (50 ml) and brine (50 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3c8387cc64ab4c5ca79129382766d3e7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003783B2

연결된 노트

불러오는 중…