Formaldehyde → 3-Benzyloxy-4-dimethylaminoestra-1,3,5(10)-trien-17-one

HRID 1003194노트

반응식

HRID 1003194 반응식
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]=O.[C:31]([BH3-])#[N:32].[Na+].[NH4+].[Cl-]>C1COCC1.CC#N>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1[N:32]([CH3:31])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydride2회HCID 54424644HCID 54424644, 화합물

생성물 1

HCID 693344893-Benzyloxy-4-dimethylaminoestra-1,3,5(10)-trien-17-one수율 54%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 3-benzyloxy-4-aminoestra-1,3,5(10)-trien-17-one (85, 0.188 g, 0.5 mmol) in THF (1.0 mL) and CH3CN (5.0 mL) were added 37% aqueous formaldehyde (1.0 mL) and sodium cyanoborohydride (0.251 g, 4.0 mmol); the mixture was then stirred for 3 h at room temperature. Additional sodium cyanoborohydride (0.251 g, 4.0 mmol) was then added, and the mixture stirred for 24 h. Saturated aqueous NH4Cl at 0° C. was added, and the mixture extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1→1:1, v/v) to afford 0.109 g of 86 (54% yield).

후처리

  1. stirringthe mixture stirred for 24 h
  2. extractionthe mixture extracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

출처 및 근거

ORD 기록
ord-f5cab91b97d5434da6ef93cc4e00ac87
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046186

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