HCID 67130065, compound → HCID 67130064, compound

HRID 1038815Notes

Reaction equation

HRID 1038815 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH2:15][CH2:14][N:13](C(OCC2C=CC=CC=2)=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[CH:27]1([CH2:26][C:10]2([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:29][CH2:28]1

Participants

4

Reactant 1

HCID 67130065HCID 67130065, compound

Product 1

HCID 67130064HCID 67130064, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In one portion, 10% Pd/C (0.159 g, 1.491 mmol) was added to a mixture of benzyl 4-((tert-butoxycarbonylamino)methyl)-4-(cyclopropylmethyl)piperidine-1-carboxylate (0.60 g, 1.5 mmol, prepared using AF from benzyl 4-cyanopiperidine-1-carboxylate [Oakwood] with (bromomethyl)cyclopropane, AE, O with Boc2O) in MeOH (50 mL) at rt. The mixture was stirred under H2 at rt overnight. The mixture was filtered and concentrated in vacuo to provide tert-butyl (4-(cyclopropylmethyl)piperidin-4-yl)methylcarbamate (0.40 g, 95%): LC/MS (Table 2, Method i) Rt=1.59 min; MS m/z: 269 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dceb02a0ada45f394a027fe50b47a0e
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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