4-Nitrobenzoic Acid → (R)-3-[(4-Nitrobenzoyl)oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

HRID 2107975Notes

Reaction equation

HRID 2107975 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C@H:14]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]#[C:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:15]1=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:48]([C:51]1[CH:59]=[CH:58][C:54]([C:55](O)=[O:56])=[CH:53][CH:52]=1)([O-:50])=[O:49]>O1CCCC1>[N+:48]([C:51]1[CH:52]=[CH:53][C:54]([C:55]([O:13][C@@H:14]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]#[C:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[C:15]2=[O:28])=[O:56])=[CH:58][CH:59]=1)([O-:50])=[O:49]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15046675(S)-3-hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Product 1

HCID 15086779(R)-3-[(4-Nitrobenzoyl)oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinoneYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.9 g of diethyl azodicarboxylate in 5 ml of tetrahydrofuran was added dropwise to a solution of 0.9 g of (S)-3-hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone, 1.1 g of triphenylphosphine and 0.9 g of 4-nitrobenzoic acid in 30 ml of dry tetrahydrofuran. The mixture was stirred overnight and the solvent was removed in vacuo. The residue was purified by chromatography (silica gel), giving 1.2 g of the desired product as off white crystals, [α]D260 =+41° (dichloromethane); mp 89°-90° C.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-23fce8a39fbb4108bfa9b9e8151d1f32
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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