Piperidine → ((S)-3-amino-4-morpholin-4-yl-4-oxobutyl)carbamic acid tert-butyl ester

HRID 1811731Notes

Reaction equation

HRID 1811731 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][CH2:8][CH2:9][C@H:10]([NH:19]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>CN(C)C=O>[C:1]([O:5][C:6](=[O:37])[NH:7][CH2:8][CH2:9][C@H:10]([NH2:19])[C:11]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 59224644[(S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-morpholin-4-yl-4-oxobutyl]carbamic acid tert-butyl ester

Product 1

HCID 59224697((S)-3-amino-4-morpholin-4-yl-4-oxobutyl)carbamic acid tert-butyl esterYield 0.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[(S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-morpholin-4-yl-4-oxobutyl]carbamic acid tert-butyl ester (172 mg, 0.338 mol) obtained in Step 1 above was dissolved in N,N-dimethylformamide (1.5 ml), and then piperidine (84 μl) was added thereto. After the solution was stirred at room temperature for 30 minutes, the solvent was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=20:1) to yield ((S)-3-amino-4-morpholin-4-yl-4-oxobutyl)carbamic acid tert-butyl ester (95 mg) as a colorless oily material.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-bccbfa6db8b7442b8e1cf2c3aa43114d
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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