HCID 56982890, compound → HCID 67852594, compound

HRID 1197924Notes

Reaction equation

HRID 1197924 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:18]C(=O)OC(C)(C)C)[CH:9]([OH:17])[CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[NH2:18][C@H:8]([CH:9]([OH:17])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 56982890HCID 56982890, compound

Product 1

HCID 67852594HCID 67852594, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

600 mg (1.69 mmol) of t-butyl [(1S)-1-(cyclohexylmethyl)-2-hydroxy-3-piperidinopropyl]carbamate were dissolved in 6 ml of 5.2N hydrochloric acid in dioxan and subsequently stirred at room temperature for 2 hours. Thereafter, the reaction solution was evaporated under reduced pressure, made alkaline with 25% ammonia solution and extracted with ether. Drying and evaporation of the ether extract yielded 400 mg (93%) of α-[(S)-1-amino-2-cyclohexylethyl]-1-piperidineethanol (αR:αS=5:1) as a resin, MS: 236 (M-H2O)+.

Workup

  1. customThereafter, the reaction solution was evaporated under reduced pressure
  2. extractionextracted with ether
  3. customDrying
  4. customevaporation of the ether
  5. extractionextract

Sources & evidence

ORD record
ord-26670447ee724ba59e781cd924fc8283
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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