Triethylamine → (S)-1-Cbz-3-Boc-Aminopiperidine

HRID 919596Notes

Reaction equation

HRID 919596 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.CCN(CC)CC.[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][C:30](Cl)=[O:31])=[CH:24][CH:23]=1>C(Cl)Cl>[C:10]([O:9][C:8]([NH:7][C@H:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:30]([O:29][CH2:28][C:25]2[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=2)=[O:31])[CH2:2]1)=[O:14])([CH3:11])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamate

Product 1

HCID 50999241(S)-1-Cbz-3-Boc-AminopiperidineYield 89.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl(S)-piperidin-3-ylcarbamate (1.0 g, 5.0 mmol) and Et3N (0.76 mL) in CH2Cl2 was added Cbz-Cl (50% solution in toluene, 5.49 mmol, 0.78 mL) at 0° C. The reaction mixture was then warmed to rt and stirred for 3 h, diluted with CH2Cl2 (50 mL) and washed with water (3×5 mL). The organic layer was then dried over Na2SO4 and concentrated in vacuo to give (1.5 g, 89%) of the titled compound which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 7.35-7.38 (m, 5H), 5.13-5.12 (d, 2H), 4.61 (bs, 1H), 3.73-3.67 (m, 2H), 3.51-3.46 (m, 2H), 3.26-2.23 (m, 2H), 1.86-1.80 (m, 2H), 1.66-1.50 (m, 1H), 1.42 (s, 9H). LC-MS: m/z [M-100]=235 & [M+23]=357.

Workup

  1. washwashed with water (3×5 mL)
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c70d16f318846f8b212e1970e4e5002
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

Loading…