2-Naphthol → tert-Butyl (R)-3-(naphth-2-yloxymethyl)pyrrolidine-1-carboxylate

반응식

[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH:23]1[C:24]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:22]=1[O:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1

참가 물질

반응물 4

HCID 86632-Naphthol

HCID 11776Triphenylphosphine

HCID 75555Diisopropyl diazene-1,2-dicarboxylate

HCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 67351381tert-Butyl (R)-3-(naphth-2-yloxymethyl)pyrrolidine-1-carboxylate수율 53.8%

실험 절차

The procedure is the same as for Example 1 (Stage 1.2) starting from 2.00 g (9.94 mmol) of tert-butyl (R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate (commercial), 2.00 g (13.91 mmol) of naphth-2-ol, 3.90 g (14.91 mmol) of triphenylphosphine and 3.01 g (14.91 mmol) of diisopropyl azodicarboxylate. 1.75 g of product are obtained in the form of an oil after purification on a column of silica gel, elution being carried out with dichloromethane.