Nitrogen → cis-1,1-Dimethylethyl [((3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamate

HRID 657135Notes

Reaction equation

HRID 657135 reaction equation
[CH3:1][C:2]([Si:5]([CH3:33])([CH3:32])[O:6][C@H:7]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[CH2:8]1)([CH3:4])[CH3:3].[H][H].N#N>CCO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:33])([CH3:32])[O:6][C@H:7]1[CH2:8][NH:9][CH2:10][C@@H:11]([CH2:13][NH:14][C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12]1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 947NitrogenHCID 131729312cis-Phenylmethyl (3rs,5rs)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 131729313cis-1,1-Dimethylethyl [((3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamateYield 102.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To cis-phenylmethyl (3RS,5RS)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (550 mg; 1.1 mmol) in EtOH (50 ml) was added Pd/C (150 mg; 10%). The reaction was hydrogenated on a Parr apparatus at 40 psi of H2 for 1.5 hours. The hydrogen was displaced with N2 and the solution was filtered through a pad of Celite® to remove the catalyst which was washed with additional EtOH (50 ml). The filtrate was then concentrated under reduced pressure to give the desired compound (390 mg; 100%) as a pale yellow oil which was used without further purification.

Workup

  1. filtrationthe solution was filtered through a pad of Celite®
  2. customto remove the catalyst which
  3. washwas washed with additional EtOH (50 ml)
  4. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc86819cdfc8497c8e6d441271b0906b
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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