Methane → HCID 12962050, compound

HRID 1065699Notes

Reaction equation

HRID 1065699 reaction equation
[CH3:1][NH:2][C@H:3]1[C@H:8]([OH:9])[CH2:7][C@H:6]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:4]12[CH3:5])[C@:18]1([CH3:19])[C:13]([CH2:14][C@@H:15]([OH:23])[CH2:16][CH2:17]1)=[CH:12][CH2:11]3.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28].C>CO>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28].[CH3:1][NH:2][C@H:3]1[C@H:8]([OH:9])[CH2:7][C@H:6]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:4]12[CH3:5])[C@:18]1([CH3:19])[C:13]([CH2:14][C@@H:15]([OH:23])[CH2:16][CH2:17]1)=[CH:12][CH2:11]3

Participants

5

Reactant 3

HCID 297MethaneHCID 444266Maleic AcidHCID 1296205117beta-Methylamino-androst-5-ene-3beta,16alpha-diol

Product 1

HCID 12962050HCID 12962050, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

17β-Methylamino-androst-5-ene-3β,16α-diol (1.15 g) was suspended in methanol (23 ml) and a solution of maleic acid (0.42 g) in methanol (4.2 ml) was added. The resulting solution was treated with charcoal, filtered and the filtrates were evaporated under reduced pressure. Crystallisation of the residue from acetone afforded pure 17β-methylamino-androst-5-ene-3β,16α-diol (Z)-2-butenedioate (1:1) (salt) as an amorphous solid (1.42 g; 90.4%), m.p. 135° C.-(softens)-145° C., [α]D -55.4° (c 0.83 in D.M.S.O.).

Workup

  1. filtrationfiltered
  2. customthe filtrates were evaporated under reduced pressure
  3. customCrystallisation of the residue from acetone afforded pure 17β-methylamino-androst-5-ene-3β,16α-diol (Z)-2-butenedioate (1:1) (salt) as an amorphous solid (1.42 g; 90.4%), m.p. 135° C.-(softens)-145° C., [α]D -55.4° (c 0.83 in D.M.S.O.)

Sources & evidence

ORD record
ord-948c2d4bd451451eba5e371f8af2510e
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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