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

HRID 15022Notes

Reaction equation

HRID 15022 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.[H][H]>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

5

Reactant 2

HCID 117387271,1-Dimethylethyl (trans)-3-hydroxy4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineYield 72.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (43) (0.028 mol) in methanol (100 ml) was hydrogenated with palladium-on-carbon (10%, 2 g) as a catalyst. After uptake of hydrogen (1 equivalent) the catalyst was filtered off and the filtrate was evaporated, yielding 4.7 g of 1,1-dimethylethyl (3S-trans)-4-(aminomethyl)-3-hydroxy-1-piperidinecarboxylate (intermediate (44); [α]D20=+4.37° (c=24.03 mg/5 ml in CH3OH)).

Workup

  1. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-215187a38156403f81f9176d9ddfd99e
Source dataset
uspto-grants-2010_06
Patent number
US07732464B2

Reaction notes

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