Piperidine → Tert-butyl [4-(glycylamino)benzyl]carbamate

HRID 1755202Notes

Reaction equation

HRID 1755202 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:37])[CH2:18][NH:19]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>CN(C=O)C>[NH2:19][CH2:18][C:17]([NH:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:15][CH:14]=1)=[O:37]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 867184019H-fluoren-9-ylmethyl {2-[(4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)amino]-2-oxoethyl}carbamate

Product 1

HCID 86718402Tert-butyl [4-(glycylamino)benzyl]carbamateYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of #B118 (7.0 g, 14.0 mmol, 1.0 eq) in DMF (70 mL) was added piperidine (4.7 mL, 47.5 mmol, 3.4 eq.) at room temperature. The mixture was stirred at room temperature for 30 min, evaporated in vacuo. The residue was washed with petroleum ether (100 mL×2) and re-crystallized from EtOAc (50 mL) and petroleum ether (200 mL) to gave #B119 (3.3 g, 84.6%) as a white solid. 1H NMR (400 Hz, CDCl3): δ 9.37 (s, 1H), 7.57 (d, 2H), 7.25 (d, 2H), 4.80 (br, 1H), 4.27 (d, 2H), 3.47 (s, 2H), 1.45 (s, 9H)

Workup

  1. customevaporated in vacuo
  2. washThe residue was washed with petroleum ether (100 mL×2)
  3. customre-crystallized from EtOAc (50 mL) and petroleum ether (200 mL)

Sources & evidence

ORD record
ord-e8d47814871f4033ad2498feb253b84f
Source dataset
uspto-grants-2015_10
Patent number
US09169264B2

Reaction notes

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