Acetic Acid → Ammonia

HRID 1829186Notes

Reaction equation

HRID 1829186 reaction equation
C(O)(=O)C.O=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:33]1[CH2:38][CH2:37][CH:36]([OH:39])[CH2:35][CH2:34]1.C(N(CC)CC)C>ClCCl>[NH3:9].[OH:39][CH:36]1[CH2:37][CH2:38][N:33]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:34][CH2:35]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 222AmmoniaHCID 9835508tert-Butyl 4-hydroxy-[1,4'-bipiperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic acid (3.25 ml, 41.3 mmol) followed by tert-butyl 4-oxo-1-piperidinecarboxylate (1 g, 5.0 mmol) and sodium triacetoxyborohydride (2.11 g, 10 mmol) were added to a solution of 4-piperidinol (757 mg, 7.5 mmol) and triethylamine (5.5 ml, 37.5 mmol) in dichloromethane (50 ml), and the reaction stirred at room temperature for 18 hours. The reaction was washed with sodium bicarbonate solution, dried (MgSO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0.5 to 93:7:0.5) to give the title compound as a clear gum, 700 mg.

Workup

  1. washThe reaction was washed with sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customThe residual oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-939db8ff44064583847b47b4ab5462eb
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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