HCID 12961935, compound → HCID 12961937, compound

HRID 1065688Notes

Reaction equation

HRID 1065688 reaction equation
[CH2:1]1[O:27][C:4]2([CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:6]([CH2:7][CH2:8][C@@H:9]4[C@@H:18]3[CH2:17][CH2:16][C@@:14]3([CH3:15])[C@H:10]4[CH2:11][C@H:12]([OH:26])[C@H:13]3[NH:23][CH:24]=O)[CH2:5]2)[O:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:2]1[O:3][C:4]2([CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:6]([CH2:7][CH2:8][C@@H:9]4[C@@H:18]3[CH2:17][CH2:16][C@@:14]3([CH3:15])[C@H:10]4[CH2:11][C@H:12]([OH:26])[C@H:13]3[NH:23][CH3:24])[CH2:5]2)[O:27][CH2:1]1

Participants

4

Reactant 2

HCID 12961935HCID 12961935, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12961937HCID 12961937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17α-formamido-16β-hydroxy-5α-androstan-3-one ethylene acetal (5.2 g) in dry tetrahydrofuran (182 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (2.6 g) in tetrahydrofuran (78 ml) at 0° C. The cooling bath was removed and the stirred suspension was heated under reflux, and under a nitrogen atmosphere for 5 h. The mixture was cooled, water was added dropwise, and the solids were removed by filtration through dicalite. The filter was washed with hot tetrahydrofuran and the combined filtrate and washings were evaporated to give 16β-hydroxy-17α-methylamino-5α-androstan-3-one ethylene acetal as a colourless residue (5.0 g.).

Workup

  1. customThe cooling bath was removed
  2. temperaturethe stirred suspension was heated
  3. temperatureunder reflux
  4. temperatureThe mixture was cooled
  5. additionwater was added dropwise
  6. customthe solids were removed by filtration through dicalite
  7. washThe filter was washed with hot tetrahydrofuran
  8. customthe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-b3dc0064b60c47448d5db98f5cc954de
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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