反応 #814045

ord-a62160e21876444f9bf22a9babde342e

反応方程式

CN1C(=O)CC[C@]2(C)[C@H]3CC[C@]4(C)C(C=NO)CC[C@H]4[C@@H]3CC[C@@H]12
( 46 )
CN1C(=O)CC[C@]2(C)[C@H]3CC[C@]4(C)C(C=NO)CC[C@H]4[C@@H]3CC[C@@H]12
4-Methyl-3-oxo-5α-4-azaandrostan-17-carboxaldehyde oxime
CCO
ethanol
CC(=O)O
acetic acid
[H][H]
hydrogen
→
CN1C(=O)CC[C@]2(C)[C@H]3CC[C@]4(C)C(CN)CC[C@H]4[C@@H]3CC[C@@H]12
( 47 )
CN1C(=O)CC[C@]2(C)[C@H]3CC[C@]4(C)C(CN)CC[C@H]4[C@@H]3CC[C@@H]12
17-Aminomethyl-4-methyl-5α-4-azaandrostan-3-one

反応物

CN1C(=O)CC[C@]2(C)[C@H]3CC[C@]4(C)C(C=NO)CC[C@H]4[C@@H]3CC[C@@H]12
( 46 )
CN1C(=O)CC[C@]2(C)[C@H]3CC[C@]4(C)C(C=NO)CC[C@H]4[C@@H]3CC[C@@H]12
4-Methyl-3-oxo-5α-4-azaandrostan-17-carboxaldehyde oxime
CCO
ethanol
CC(=O)O
acetic acid
[H][H]
hydrogen

試薬

[O]=[Pt]=[O]
PtO2

溶媒

O
water

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The filtered reaction mixture
  2. 2
    濃縮was concentrated in vacuo
  3. 3
    洗浄the chloroform solution washed with fresh dilute sodium hydrogen carbonate solution
  4. 4
    乾燥dried (Na2SO4)
  5. 5
    その他obtained with hexane containing a small amount of ether

実験手順

A mixture of (46) (0.67 g, 2.0 mM), ethanol (100 mL), glacial acetic acid (8 mL) and water (4 mL) was reduced in a hydrogen atmosphere (40 p.s.i.) at room temperature in the presence of PtO2 until TLC analysis indicated complete reduction. The filtered reaction mixture was concentrated in vacuo, the residue taken up in chloroform, and the chloroform solution washed with fresh dilute sodium hydrogen carbonate solution and dried (Na2SO4). Concentration of the filtered chloroform solution followed by trituration of the residue obtained with hexane containing a small amount of ether yielded (47) as an off-white solid. MS MH+ calcd for C20H34N2O 318.49, observed m/e 319.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05710275uspto-grants-1998_01