Isopropanol → 3-Hydroxyandrostane-17-carbonitrile

HRID 267626노트

반응식

HRID 267626 반응식
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)#[N:2].C(O)(C)C.C(N(CC)CC)C>O>[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)#[N:2]

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 86733140HCID 86733140, 화합물

생성물 1

HCID 1710843-Hydroxyandrostane-17-carbonitrile

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 17β-cyano-5α-androstan-3-one (1.0 g.) in the minimum volume of isopropanol (ca. 75 ml.) was added to a stock solution of chloroiridic acid/trimethyl phosphite complex (50 ml.) preneutralised to pH4 with triethylamine (4 ml.). This solution, after being refluxed for 20 hours, was poured into water (200 ml.) and extracted with chloroform. The chloroform solution was washed with water, dried (MgSO4), filtered and evaporated to a gum (1.13 g.). This was subjected to preparative t.l.c. eluting successively with ethanol/chloroform (1:49) and ethyl acetate/benzene (1:19). The main band was removed between the eluant change and the final elution was repeated four times before removing the main band. This gave pure title compound (195 mg.) as a white solid; m.p. 156°-159°; [α]D + 56° (c 0.4%).

후처리

  1. temperatureThis solution, after being refluxed for 20 hours
  2. extractionextracted with chloroform
  3. washThe chloroform solution was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a gum (1.13 g.)
  7. washeluting successively with ethanol/chloroform (1:49) and ethyl acetate/benzene (1:19)
  8. customThe main band was removed between the eluant change
  9. washthe final elution
  10. custombefore removing the main band
  11. custom[α]D + 56° (c 0.4%)

출처 및 근거

ORD 기록
ord-27f4976f2d5c4dda9bd01518dea0c083
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03943124

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