N-Hydroxyphthalimide → HCID 67681828, compound

HRID 439883Notes

Reaction equation

HRID 439883 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([NH:20][C@@H:21]1[CH2:25][CH2:24][C@H:23]([CH2:26][OH:27])[CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O[N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[C:13]([NH:20][C@@H:21]1[CH2:25][CH2:24][C@H:23]([CH2:26][O:27][N:29]2[C:33](=[O:34])[C:32]3[C:31](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:30]2=[O:39])[CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11962831tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

Product 1

HCID 67681828HCID 67681828, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2.94 ml (0.01755 mol) of diethyl azodicarboxylate (93%) in 10 ml of benzene is added dropwise to a mixture of 3.6 g (0.01672 mol) of cis-3-(N-BOC-amino)-cyclopentanemethanol, 2.73 g (0.01673 mol) of N-hydroxyphthalimide, 4.49 g (0.01672 mol) of triphenylphosphine and 60 ml of benzene at 20°-30° C., while stirring. After the mixture has been stirred at room temperature for 1 hour, the precipitate formed during the reaction is filtered off, the residue on the filter is suspended in benzene and the suspension is filtered again. The latter operation is repeated twice more (residue on the filter: diethyl 1,2-hydrazinedicarboxylate), and the resulting filtrates are combined and these are evaporated in vacuo. Purification of the residue is carried out by means of flash chromatography on silica gel using ethyl acetate/hexane mixtures (1:3 and 1:1). The title compound is thus obtained, m.p. 162°-163° C.

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 1 hour
  2. customthe precipitate formed during the reaction
  3. filtrationis filtered off
  4. filtrationthe suspension is filtered again
  5. filtrationfilter
  6. customthese are evaporated in vacuo
  7. customPurification of the residue

Sources & evidence

ORD record
ord-668029e5381f4a3986f61ab340f1349e
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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