Methanol → HCID 12836865, compound

HRID 848784Notes

Reaction equation

HRID 848784 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20]N1C(=O)CCC1=O.O[C@H:29]1[CH2:46][CH2:45][C@@:44]2([CH3:47])[C@@H:31]([CH2:32][CH2:33][C@@H:34]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@H:35]3[CH2:36][CH2:37][C@@H:38]2[O:48][CH3:49])[CH2:30]1.CO>C1COCC1>[Cl:20][C@@H:29]1[CH2:46][CH2:45][C@@:44]2([CH3:47])[C@@H:31]([CH2:32][CH2:33][C@@H:34]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@H:35]3[CH2:36][CH2:37][C@@H:38]2[O:48][CH3:49])[CH2:30]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 31398Chlorosuccinimide2×HCID 12836862HCID 12836862, compound

Product 1

HCID 12836865HCID 12836865, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphine (8.22 g.) in THF (80 ml.) is added dropwise to N-chlorosuccinimide (4.18 g.) with stirring and cooling so that the temperature remains below 30°. A solution of 3β-hydroxy-17β-methoxy-5α-androstane (Example 27, 4.8 g.) in THF (50 ml.) is slowly added to the N-chlorosuccinimide mixture. After 2 hours, methanol is added and the mixture is filtered to obtain the title compound (recrystallized from acetone): m.p. 151°-154°; NMR (CDCl3) 0.74, 0.78, 3.20, 3.33 and 4.47 δ; MS (m/e) 324, 309, 277 and 251.

Workup

  1. temperaturecooling so that the temperature
  2. customremains below 30°
  3. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-95a2c3f78b5b4876bd6c673f1befd4c0
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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