Carbonic acid, bis(1,1-dimethylethyl) ester → Tert-butyl (1-benzyl-4-hydroxy-4-piperidinyl)methylcarbamate

HRID 1972057Notes

Reaction equation

HRID 1972057 reaction equation
[NH2:1][CH2:2][C:3]1([OH:16])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.[C:17]([O:21][C:22](=O)[O:23]C(C)(C)C)([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:17]([O:21][C:22](=[O:23])[NH:1][CH2:2][C:3]1([OH:16])[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 104210264-(Aminomethyl)-1-benzylpiperidin-4-ol

Product 1

HCID 11759029Tert-butyl (1-benzyl-4-hydroxy-4-piperidinyl)methylcarbamateYield 36.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-aminomethyl-1-benzyl-piperidin-4-ol (264 mmol, 58 g) in DCM (200 mL) and saturated NaHCO3 (200 mL) was added di-tert-butylcarbonate (396 mmol, 86.4 g). The reaction mixture was stirred for 12 hours. The layers were separated and the organic layer was washed with brine (50 mL) and evaporated. The product was purified on 1 L of SiO2 using a mixtures of ethyl acetate and DCM to give (1-benzyl-4-hydroxy-piperidin-4-ylmethyl)-carbamic acid tert-butyl ester (31 g).

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine (50 mL)
  3. customevaporated
  4. customThe product was purified on 1 L of SiO2 using a mixtures of ethyl acetate and DCM

Sources & evidence

ORD record
ord-fb0ae1fb15564c21ad1059ec25ac1ec6
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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