N-Hydroxyphthalimide → HCID 22408674, compound

HRID 439891Notes

Reaction equation

HRID 439891 reaction equation
[C:1]([NH:8][CH2:9][CH:10]1[CH2:13][CH:12]([OH:14])[CH2:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(OCC)(=O)C.CCCCCC>[C:1]([NH:8][CH2:9][CH:10]1[CH2:13][CH:12]([O:14][N:16]2[C:20](=[O:21])[C:19]3[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]2=[O:26])[CH2:11]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22408693tert-Butyl [(3-hydroxycyclobutyl)methyl]carbamate

Product 1

HCID 22408674HCID 22408674, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Analogously to Example 1 b, but using ethyl acetate/hexane mixtures (1:3 and 1:1) in the flash chromatography, starting from 15.24 g (0.0757 mol) of 3-(N-BOC-aminomethyl)-cyclobutanol, 12.35 g (0.0757 mol) of N-hydroxyphthalimide, 19.85 g (0.0757 mol) of triphenylphosphine and 13.3 ml (0.0795 mol) of diethyl azodicarboxylate (93%), the title compound, which melts at 161°-162° C. after recrystallization from ethyl acetate, is obtained. Evaporation of the mother liquor and recrystallization of the residue from ethyl acetate/hexane gives a further batch of the title compound, m.p. 145°-150° C.

Workup

  1. customthe title compound, which melts at 161°-162° C. after recrystallization from ethyl acetate
  2. customis obtained
  3. customEvaporation of the mother liquor and recrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-05a918a5a12f4cc5ac61fafce0369e1e
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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