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

HRID 2168779Notes

Reaction equation

HRID 2168779 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-b76c8aabfbc84270b7752213d311ad1c
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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