HCID 22844620, compound → HCID 22844608, compound

HRID 1720654Notes

Reaction equation

HRID 1720654 reaction equation
C(OC([N:11]1[C@@H:15]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:14]([CH:23]([OH:31])[CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[O:13]C1(C)C)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@@H:15]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:14]([OH:13])[CH:23]([OH:31])[CH2:24][N:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 1

HCID 22844620HCID 22844620, compound

Product 1

HCID 22844608HCID 22844608, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

71 mg of (4S,5RS)-3-benzyloxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-5-[(1RS)-1-hydroxy-2piperidinoethyl]oxazolidine was dissolved in 1.5 ml of ethanol, and palladium black was added thereto. Then, hydrogenation was conducted at room temperature under atmospheric pressure. The catalyst was removed by filtration, and then the solvent was distilled off under reduced pressure to obtain 41 mg of (2RS,3RS,4S)-4-amino-5-cyclohexyl-1-piperidino-2,3-pentanediol as colorless oily substance.

Workup

  1. customwas conducted at room temperature under atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-084b7fa98083469e828451f6d8c06718
Source dataset
uspto-grants-1996_04
Patent number
US05506356

Reaction notes

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