Methyl p-toluenesulfonate → HCID 22135134, compound

HRID 1826597Notes

Reaction equation

HRID 1826597 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].S(C1C=CC(C)=CC=1)(O[CH3:32])(=O)=O.C(=O)(O)[O-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:32][N:11]([CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

7

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 117920261-N-Boc-4-(N-cbz-aminomethyl)piperidine

Product 1

HCID 22135134HCID 22135134, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-(benzyloxycarbonylaminomethyl)-1-Boc-piperidine (0.360 g, 1.03 mol) in DMF (10 mL) was treated with sodium hydride (60%, 0.050 g, 1.25 mmol). After 0.5 h, methyl tosylate (0.18 mL, 1.20 mmol) was added and the mixture heated to 60° C. After 12 h, the mixture was poured into EtOAc and saturated aqueous sodium bicarbonate. The combined extracts were washed with water, brine and concentrated to afford 0.300 g (79%) the title compound which was used without further purification.

Workup

  1. waitAfter 12 h
  2. washThe combined extracts were washed with water, brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-700d9f6cb2174014a080f2c626b2992d
Source dataset
uspto-grants-2006_05
Patent number
US07053078B2

Reaction notes

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