Piperidine → HCID 9867118, compound

HRID 895841Notes

Reaction equation

HRID 895841 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C@H:16]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[CH:18]([CH2:19][CH2:20][C:21]3[C:22]4[C@:30]([CH3:38])([CH2:31][CH2:32][C:33]=32)[C@@H:25]([C@H:26]([CH3:29])[CH:27]=O)[CH2:24][CH:23]=4)[C:17]1([CH3:40])[CH3:39].[NH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:41]1([CH2:29][C@H:26]([C@@H:25]2[C@:30]3([CH3:38])[C:22]([C:21]4[CH2:20][CH2:19][C@@H:18]5[C@:34]([C:33]=4[CH2:32][CH2:31]3)([CH3:37])[CH2:35][CH2:36][C@H:16]([OH:15])[C:17]5([CH3:40])[CH3:39])=[CH:23][CH2:24]2)[CH3:27])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11772697HCID 11772697, compound

Product 1

HCID 9867118HCID 9867118, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

38 mg sodium tris(acetoxy)borohydride were added to a solution of 42 mg (20S)-3β-hydroxy-4,4,20-trimethyl-pregna-8,14-dien-21-al and 10 μl piperidine in 3 ml tetrahydrofuran at room temperature. The mixture was stirred for two hours, poured into saturated sodium bicarbonate solution, extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 15 mg (20S)-20-[(piperidin-1-yl)methyl]-4,4-dimethyl-5α-pregna-8,14-dien-3β-ol as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-492d3799c1ca43b48c841e4b3257cfad
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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