Methanol → HCID 15172765, compound

HRID 1014943Notes

Reaction equation

HRID 1014943 reaction equation
[C:1]1([CH2:7][C@H:8]([OH:12])[C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:13]#[N:14].[K+].[C:16]([O-:19])(=O)[CH3:17].[NH4+].[CH3:21]O>>[OH:12][C@@H:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]([N:14]1[CH2:17][CH2:16][O:19][CH2:21][CH2:13]1)=[O:11]

Participants

5

Reactant 4

HCID 887MethanolHCID 9032Potassium CyanideHCID 4447183-Phenyllactic acid, (S)-HCID 517165Ammonium Acetate

Product 1

HCID 15172765HCID 15172765, compoundYield 98%

Procedure

1-Boc-4-piperidone 1 (2 g, 10 mmol) is added to a flask of KCN (3.256 g, 50 mmol) and ammonium acetate (7.7 g, 100 mmol). The flask is capped with a rubber septum and dry methanol (50 mL) is added via syringe. The reaction is sonicated for 15 minutes to break up the salts and then stirred at room temperature overnight. The volatiles are removed by rotary evaporation and the resulting residue is neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organics are dried over MgSO4 and the solvent is removed to afford 2.21 g, 98% yield of pure 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester 2. 1H NMR (CDCl3, 400 MHz) δ 3.95 (s, 2H), 3.18 (t, J=11.3 Hz, 2H), 1.96 (d, J=13.2 Hz, 2H), 1.82 (s, 2H), 1.63 (t, J=12 Hz, 2H), 1.45 (s, 9H).

Workup

  1. additionis added via syringe
  2. customThe reaction is sonicated for 15 minutes
  3. customThe volatiles are removed by rotary evaporation
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organics are dried over MgSO4
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-ff33c8672f7b4c3dbf3d303e5b226da7
Source dataset
uspto-grants-2011_07
Patent number
US07985749B2

Reaction notes

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