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HRID1077594

反应详情

EQUATION

反应方程式

HRID 1077594 的结构方程式

REACTANTS

反应物

3
结构：O
HCID962

Water

H2O

结构：[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-].c1cc[nH+]cc1.c1cc[nH+]cc1
HCID2724130

Chromic acid (H2Cr2O7), compd. with pyridine (1:2)

C10H12Cr2N2O7

结构：CC(C)CC(O)[C@H]1CC[C@H]2[C@@H]3CN(C(C)(C)C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12CC(=O)O
HCID86749708

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)CC(=O)[C@H]1CC[C@H]2[C@@H]3CN(C(C)(C)C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12CC(=O)O
HCID86749709

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A solution of 17β-(1-hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one (160 mg, 0.349 mmol) prepared in part C above, in DMF (10 mL) is treated with pyridinium dichromate (656 mg, 1.74 mmol) at room temperature. After 10 hrs the reaction is poured into water, extracted with ethyl acetate (2×50 mL), the extracts are dried over MgSO4, concentrated and chromatographed on silica gel (40% ethyl acetate/hexanes) to give crude 17β-(1 -oxo-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one; yield: 135 mg (85%). A portion of this material (81 mg, 0.18 mmol) is treated with trifluoroacetic acid as described in Example 4 above to give, after recrystallization from diethyl ether/hexanes 17β-(1-oxo-3-methylbutyl)-6-azaandrost-4-en-3-one as a white crystalline solid; yield: 58 mg (92%); m.p. 169°-171° C. Anal. Calcd. for C23H35NO2 ·1/4H2O; C, 76.30; H, 9.88; N, 3.87. Found: C, 76.48; h, 9.93; N, 3.89.

WORKUP

后处理

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialthe extracts are dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel (40% ethyl acetate/hexanes)