1,1-Dimethylethyl (trans)-3-hydroxy4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate → trans-1-Boc-4-aminomethyl-3-hydroxypiperidine

HRID 559130Notes

Reaction equation

HRID 559130 reaction equation
[OH:1][C@H:2]1[C@H:7]([CH2:8][NH:9]CC2C=CC=CC=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1>CO.[Pd]>[NH2:9][CH2:8][C@@H:7]1[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:3][C@H:2]1[OH:1]

Participants

4

Reactant 1

HCID 117387271,1-Dimethylethyl (trans)-3-hydroxy4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate

Product 1

HCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (1-d) (max. 0.023 mol crude residue) in methanol (100 ml) was hydrogenated with palladium-on-carbon (10%, 1 g) as a catalyst. After uptake of H2 (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was solidified in DIPE+ACN, filtered off and dried (vacuum, 40° C.), yielding 4 g (76%) of 1,1-dimethylethyl (trans)-4-(aminomethyl)-3-hydroxy-1-piperidinecarboxylate (intermediate 1-e, mp. 178° C.).

Workup

  1. filtrationAfter uptake of H2 (1 equivalent), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationfiltered off
  4. customdried (vacuum, 40° C.)

Sources & evidence

ORD record
ord-522d44a712d441b18781e53bb6095c26
Source dataset
uspto-grants-2011_11
Patent number
US08063070B2

Reaction notes

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