Benzylamine → Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate

HRID 2174962Notes

Reaction equation

HRID 2174962 reaction equation
C(OC([C:6]1[CH2:7][CH2:8][N:9]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10][C:11]=1[NH:12][CH2:13]C1C=CC=CC=1)=O)C.C(OC(C1CCN(C(OC(C)(C)C)=O)CC1=O)=O)C.C(N)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:23]([O:22][C:20]([N:9]1[CH2:8][CH2:7][CH:6]2[CH:11]([NH:12][CH2:13]2)[CH2:10]1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylateHCID 670868445-Benzylamino-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylateYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Benzylamino-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester. 3-Oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (8.15 g, 30 mmol) from Step A and benzyl amine (3.43 g, 31.8 mmol) were dissolved into toluene (150 mL). The mixture was refluxed vigorously for 72 h and the generated water was collected into Dean-Stark apparatus. The residual solution was concentrated to yield the title compound (10.2 g, 92.5%). MS (ESI) mass calcd. for C20H28N2O4, 360.45, m/z found, 361.2 [M+H]+. The crude product was carried to the next step without any purification.

Workup

  1. temperatureThe mixture was refluxed vigorously for 72 h
  2. customthe generated water was collected into Dean-Stark apparatus
  3. concentrationThe residual solution was concentrated

Sources & evidence

ORD record
ord-c50cef8f3b7a44b9b2b5360b654476e3
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

Loading…