N-Hydroxyphthalimide → HCID 67823271, compound

HRID 1109762Notes

Reaction equation

HRID 1109762 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10][C@@H:9]1[CH2:15][CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[C:1]([N:8]1[CH2:13][CH2:12][C@H:11]([O:14][N:18]2[C:22](=[O:23])[C:21]3[C:20](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]2=[O:28])[CH2:10][C@@H:9]1[CH2:15][CH3:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67823181HCID 67823181, compound

Product 1

HCID 67823271HCID 67823271, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A suspension of 0.74 g (0.003227 mol) of trans-N-BOC-2-ethyl-4-hydroxypiperidine (cf. Example 3b), 0.526 g (0.003227 mol) of N-hydroxyphthalimide and 0.846 g (0.003227 mol) of triphenylphosphine in 10 ml of benzene is reacted in accordance with the general procedure of Example 3a with a solution of 0.566 ml (0.003385 mol) of diethyl azodicarboxylate (93%) in 2 ml of benzene, to give the title compound as a colourless resin; Rf =0.60 (silica gel/ethyl acetate:hexane (2:1)).

Sources & evidence

ORD record
ord-bc7b5599168048fd8c827b185b38700b
Source dataset
uspto-grants-1994_06
Patent number
US05322852

Reaction notes

Loading…