Methylparaben → methyl 4-((2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoate

HRID 1372582Notes

Reaction equation

HRID 1372582 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([O:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[CH2:24][C@H:23]1[CH2:38][OH:39])=[O:21])([CH3:18])([CH3:17])[CH3:16].O[C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([O:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)[CH2:24][C@H:23]1[CH2:38][O:39][C:41]1[CH:50]=[CH:49][C:44]([C:45]([O:47][CH3:48])=[O:46])=[CH:43][CH:42]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67405321(2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol

Product 1

HCID 16093646methyl 4-((2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoateYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (0.37 ml, 1.86 mmol) was added to a solution of (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol (640 mg, 1.86 mmol), methyl 4-hydroxybenzoate (283 mg, 1.86 mmol) and triphenylphosphine (488 mg, 1.86 mmol) in THF (18 ml) under stirring at room temperature in a nitrogen gas stream. The reaction mixture was stirred overnight at room temperature. The residue obtained by concentrating the reaction mixture under reduced pressure was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from hexane/ethyl acetate (2/1) eluate fractions, the title compound (830 mg, 93%) was obtained as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customThe residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. customwas purified by chromatography on a silica gel column (silica gel: 100 g), whereby from hexane/ethyl acetate (2/1) eluate fractions

Sources & evidence

ORD record
ord-fc4d040097084cdeb4bafdfc1495e164
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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