Tetrahydrofuran → tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidine-1-carboxylate

HRID 1425136Notes

Reaction equation

HRID 1425136 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][CH2:17][CH3:18].C(=O)(O)[O-].[Na+].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].C1COCC1>O>[CH2:28]([O:27][C:25]([NH:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]1[O:15][CH2:16][CH2:17][CH3:18])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67548306Tert-butyl cis(+/-)-4-amino-3-propoxypiperidine-1-carboxylate

Product 1

HCID 86648603tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidine-1-carboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same operation as in Example (103a) was performed using tert-butyl cis(±)-4-amino-3-propoxypiperidine-1-carboxylate obtained in Example (113d) (3.41 g, 13.2 mmol), sodium bicarbonate (1.26 g, 15 mmol), benzyl chloroformate (2.81 g, 16 mmol), THF (15 mL) and water (15 mL). The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1) to obtain 5.14 g of the title compound as a colorless oily substance (99%).

Workup

  1. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1)

Sources & evidence

ORD record
ord-ea09d5d0a88741d098d52c27be019292
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

Loading…