N-Hydroxyphthalimide → HCID 57461145, compound

HRID 2066840Notes

Reaction equation

HRID 2066840 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].O[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:25]=[C:16]1[C:17]2[C:18](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:20])[N:15]1[O:13][CH:10]1[CH2:9][CH2:8][N:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylate

Product 1

HCID 57461145HCID 57461145, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxy-piperidine-1-carboxylic acid isopropyl ester (3.09 g, 17 mmol), N-hydroxyphthalimide (2.69 g, 17 mmol), and triphenylphosphine (4.32 g, 17 mmol) were combined in THF (30 mL). DEAD (2.6 mL, 17 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was then concentrated under vacuum and the residue was purified by flash LC(elution with 10-50% ethyl acetate and 0.1% TEA in hexanes) to afford 3.31 g (60%) of 2a as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.85-7.81 (m, 2 H), 7.83-7.29 (m, 2 H), 4.91 (quintet, J=6.3 Hz, 1 H), 4.43 (septet, J=3.9 Hz, 1 H), 3.94-3.86 (m, 2 H), 3.32-3.23 (m, 2 H), 1.99-1.78 (m, 4 H), 1.24 (d, J=6.6 Hz, 6 H); LC-MS 333.1 (MH+).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. customthe residue was purified by flash LC(elution with 10-50% ethyl acetate and 0.1% TEA in hexanes)

Sources & evidence

ORD record
ord-11ab01fdbcaf4ff1b90b2381a3866fbb
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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