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

HRID 919578Notes

Reaction equation

HRID 919578 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.O>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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamate

Product 1

HCID 50999241(S)-1-Cbz-3-Boc-AminopiperidineYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl piperidin-3-ylcarbamate (5 g, 24.9 mmol) and Et3N (3.8 mL, 27.4 mmol) in CH2Cl2 (75 mL) was added Cbz-Cl (3.92 mL, 27.4 mmol) at 0° C., after the addition was complete the reaction was warmed to rt and stirred for 4 h. The reaction was diluted with ice cooled water (30 mL) and the CH2Cl2 layer was separated and dried over Na2SO4 and concentrated in vacuo to give (7.5 g, 89%) of the tilted compound. 1H NMR (400 MHz, CDCl3): δ 7.40-7.24 (m, 5H), 5.18 (s, 2H), 4.58 (bs, 1H), 3.80-3.62 (m, 2H), 3.55-3.41 (m, 1H), 3.37-3.21 (m, 2H), 1.82-1.78 (m, 1H), 1.75-1.69 (m, 1H), 1.61-1.53 (m, 2H), 1.42 (s, 9H). ES-MS: m/z [M+1]=335.

Workup

  1. additionafter the addition
  2. additionThe reaction was diluted with ice
  3. customthe CH2Cl2 layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-880e740d62ca4faf840f962149e658af
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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