Piperidine → HCID 117749112, compound

HRID 1775885Notes

Reaction equation

HRID 1775885 reaction equation
C1C2C(COC([NH:18][C@@H:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][C:21](=[O:24])[NH:22][CH3:23])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)Cl>[CH3:23][NH:22][C:21](=[O:24])[CH2:20][C@H:19]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[NH2:18]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 117748918HCID 117748918, compound

Product 1

HCID 117749112HCID 117749112, compoundYield 226.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N4-methyl-D-asparaginate (200 mg, 0.47 mmol) in DCM (0.93 mL) was added piperidine (233 μL, 2.35 mmol). The reaction mixture was stirred at room temperature for 1 h. All solvent was removed to give 215 mg of tert-butyl N4-methyl-D-asparaginate as a mixture with 1-((9H-fluoren-9-yl)methyl)piperidine. The mixture was used without purification in the next reaction. LCMS-ESI (m/z) calculated for C9H18N2O3: 202.1. found 203.1 [M+H]+, tR=0.534 min (Method 16).

Workup

  1. customAll solvent was removed

Sources & evidence

ORD record
ord-c187dac5ddd5449aae73c5ded1418ae7
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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