Triethylamine → Tert-butyl 4-(6-hydroxybenzo[d]oxazole-2-carboxamido)piperidine-1-carboxylate

HRID 1878800Notes

Reaction equation

HRID 1878800 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]=[C:7]([C:9]([OH:11])=O)[O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:44][CH:45]1[CH2:50][CH2:49][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][CH2:46]1>CN(C)C=O>[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]=[C:7]([C:9]([NH:44][CH:45]3[CH2:46][CH2:47][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:49][CH2:50]3)=[O:11])[O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 579510576-Hydroxybenzo[d]oxazole-2-carboxylic acid

Product 1

HCID 57951081Tert-butyl 4-(6-hydroxybenzo[d]oxazole-2-carboxamido)piperidine-1-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 6-hydroxybenzo[d]oxazole-2-carboxylic acid (0.15 g, 0.86 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added triethylamine (0.10 g, 0.99 mmol), 1-hydroxybenzotriazole hydrate (0.14 g, 0.99 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.20 g, 0.99 mmol), and tert-butyl 4-aminopiperidine-1-carboxylate (0.20 g, 0.99 mmol). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue obtained was purified by flash chromatography (silica gel, ethyl acetate/hexanes=1/1) to afford tert-butyl 4-(6-hydroxybenzo[d]oxazole-2-carboxamido)piperidine-1-carboxylate as a off-white solid (0.16 g, 52%). 1H-NMR (DMSO-d6, 300 MHz): δ 10.10 (s, 1H), 9.04 (m, 1H), 7.63 (m, 1H), 7.10 (m, 1H), 7.27 (m, 5H), 6.91 (m, 1H), 3.92 (m, 3H), 2.78 (m, 2H), 1.72 (m, 2H), 1.49 (m, 2H), 1.38 (s, 9H); MS (ESI): 362.1 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by flash chromatography (silica gel, ethyl acetate/hexanes=1/1)

Sources & evidence

ORD record
ord-df9574150b96410ab1c2805d72eca981
Source dataset
uspto-grants-2012_11
Patent number
US08314107B2

Reaction notes

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