Acetic Acid → HCID 68433175, compound

HRID 1867425Notes

Reaction equation

HRID 1867425 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:19][C:20](=[O:25])[NH:21][CH2:22][CH2:23][NH2:24])([CH3:18])([CH3:17])[CH3:16].[C:26]([OH:29])(=O)[CH3:27].[BH-](OC(C)=O)(OC(C)=O)O[C:32](C)=O.[Na+].C([O-])(O)=O.[Na+].[Cl-]>C(Cl)Cl>[C:15]([O:19][C:20](=[O:25])[NH:21][CH2:22][CH2:23][N:24]([C:26](=[O:29])[CH:27]=[CH2:32])[CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)([CH3:18])([CH3:16])[CH3:17]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 312ChlorideHCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 68433175HCID 68433175, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzylpiperidone (5 g, 26 mmol) and (2-amino-ethyl)-carbamic acid tert-butyl ester (4.23 g, 26 mmol) and acetic acid (2.5 ml, 53 mmol) in CH2Cl2 (50.0 ml) was slowly added NaBH(OAc)3 (6.69 g, 32 mmol). On completion of the addition the reaction was stirred for 0.5 h. Saturated NaHCO3 (30 ml) was then cautiously added until the pH was basic. A solution of acrolyl chloride (2.3 ml, 29 mmol) in CH2Cl2 (10.0 ml) was then added and the reaction stirred for a further 1 h. The organic layer was then separated, dried (Na2SO4) and concentrated. The product was isolated by flash column chromatography (EtOAc) to afford the title compound as a light yellow foam (6 g, 58%). MS: 388.2 (MH+).

Workup

  1. additionOn completion of the addition the reaction
  2. stirringthe reaction stirred for a further 1 h
  3. customThe organic layer was then separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product was isolated by flash column chromatography (EtOAc)

Sources & evidence

ORD record
ord-ce8adae7ec014c5bb7c9913f5dd2a8bc
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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