Acetic Anhydride → HCID 70501729, compound

HRID 543645Notes

Reaction equation

HRID 543645 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N:8]1([C@H:14]2[CH2:19][C@H:18]3[C@H:20]4[C@H:30]([CH2:31][CH2:32][C@:16]3([CH3:17])[C@H:15]2[OH:34])[C@:28]2([CH3:29])[C@H:23]([CH2:24][CH2:25][C@@H:26]([OH:33])[CH2:27]2)[CH2:22][CH2:21]4)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>N1C=CC=CC=1>[C:1]([O:34][C@H:15]1[C@@H:14]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:19][C@H:18]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:16]12[CH3:17])[C@:28]1([CH3:29])[C@H:23]([CH2:24][CH2:25][C@@H:26]([OH:33])[CH2:27]1)[CH2:22][CH2:21]3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70502497HCID 70502497, compound

Product 1

HCID 70501729HCID 70501729, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (5.25 ml) was added dropwise to a stirred solution of 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol (14.0 g) in pyridine (280 ml) maintaining the temperature below 5° C. by means of an ice-bath. When the addition was complete, the cooling bath was removed. After 2 h, saturated sodium carbonate solution (approx. 120 ml) was added to give pH >7 and the precipitated product was extracted into dichloromethane (100 ml). The extract was washed with water (3×200 ml), dried (MgSO4) and evaporated to dryness. Crystallisation of the residue from acetone afforded 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol 17-acetate (14.38 g), m.p. 239°-240° C.; [α]D +25.5° C. (c 0.53 in CHCl3).

Workup

  1. temperaturemaintaining the temperature below 5° C. by means of an ice-bath
  2. additionWhen the addition
  3. customthe cooling bath was removed
  4. additionsaturated sodium carbonate solution (approx. 120 ml) was added
  5. customto give pH >7
  6. extractionthe precipitated product was extracted into dichloromethane (100 ml)
  7. washThe extract was washed with water (3×200 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness
  10. customCrystallisation of the residue from acetone

Sources & evidence

ORD record
ord-85407af1b78c4ed48e0d2e762608cd7c
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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