tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate → tert-Butyl 4-(2-aminoethyl)-4-hydroxypiperidine-1-carboxylate

HRID 471207Notes

Reaction equation

HRID 471207 reaction equation
[C:1]([CH2:3][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].[H][H]>C(O)C.C(O)(=O)C.[Pt](=O)=O>[NH2:2][CH2:1][CH2:3][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 25067313tert-Butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 45789931tert-Butyl 4-(2-aminoethyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-(cyanomethyl)-4-hydroxypiperidine-1-carboxylate (example 89, step a) (1.4 g) in a mixture of ethanol (20 mL) and acetic acid (20 mL) was hydrogenated at 4 atmospheres pressure of hydrogen in the presence of platinum(IV) oxide (0.25 g) for 4 hours. The catalyst was filtered off and the solvents removed under reduced pressure. The residue was partitioned between dilute aqueous NaOH and ethyl acetate and the organic layer dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 1.1 g. Used directly.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvents removed under reduced pressure
  3. customThe residue was partitioned between dilute aqueous NaOH and ethyl acetate
  4. dry with materialthe organic layer dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-7f3051fd28274761aaa67addb4caaf2d
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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