cis-Tert-butyl 4-(benzyloxycarbonylamino)-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylate → cis-Tert-butyl 4-amino-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylate

HRID 56420Notes

Reaction equation

HRID 56420 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]1[NH:25][C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[O:27])=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)(C)C>[NH2:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]1[NH:25][C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[O:27]

Participants

5

Reactant 2

HCID 131736928cis-Tert-butyl 4-(benzyloxycarbonylamino)-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 131736929cis-Tert-butyl 4-amino-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylateYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of cis-tert-butyl 4-(benzyloxycarbonylamino)-3-((2-(trimethylsilyl)ethoxy)carbonylamino)piperidine-1-carboxylate (1.8 g, 3.6 mmol) and 10% palladium on carbon (180 mg) in isopropanol (60 mL) was stirred under 1 atm hydrogen atmosphere (hydrogen balloon) at room temperature for 3 hours. After that, the mixture was filtered through a pad of celite. The filtrate was concentrated and purified by silica gel column chromatography (methanol/dichloromethane=1/30 to 1/10) to afford the title compound (800 mg, 61%) as a yellow oil. MS (ES+) C16H33N3O4Si requires: 359, found: 360 [M+H]+.

Workup

  1. filtrationAfter that, the mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (methanol/dichloromethane=1/30 to 1/10)

Sources & evidence

ORD record
ord-cc28b8a6b91a4e9fb38fcc2686ab3cb3
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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