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HRID1077593

反应详情

EQUATION

反应方程式

HRID 1077593 的结构方程式

REACTANTS

反应物

2
结构：CC(C)(C)N1C[C@H]2[C@@H]3CC[C@H](C=O)[C@@]3(CC(=O)O)CC[C@@H]2[C@@]2(C)CCC(=O)C=C12
HCID86749707

未命名化合物

结构：CC(C)C[Mg]Br
HCID178418816

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
HCID86749708

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A solution of 17β-formyl-6-t-butylcarboxy-6-azaandrost-4-en-3-one (550 mg, 1.37 mmol), prepared in part B above, in THF (10 mL) is treated with isobutylmagnesium bromide (2.0M in diethyl ether, 2.0 mL, 4.0 mmol) at 0° C. After 20 minutes the reaction is quenched with saturated aqueous NaHSO4, extracted with ethyl acetate (2×40 mL), dried over MgSO4, concentrated and chromatographed on silica gel (50% ethyl acetate/hexanes) to give crude 17β-(1-hydroxy-3-methylbutyl)-6-t-butylcarboxy-6-azaandrost-4-en-3-one of sufficient purity to carry on to the following steps; yield: 168 mg (26%); FAB mass spec. MH+ 460.

WORKUP

后处理

  1. customAfter 20 minutes the reaction is quenched with saturated aqueous NaHSO4
  2. extractionextracted with ethyl acetate (2×40 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed on silica gel (50% ethyl acetate/hexanes)