2-Naphthol → HCID 67349749, compound

HRID 1466004Notes

Reaction equation

[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

Participants

Reactant 4

HCID 86632-Naphthol

HCID 11776Triphenylphosphine

HCID 75555Diisopropyl diazene-1,2-dicarboxylate

HCID 1514341tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 67349749HCID 67349749, compoundYield 86%

Procedure

The procedure is the same as for Example 1 (Stage 1.2) starting from 2.00 g (9.94 mmol) of tert-butyl (S)-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. 2.80 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.

Sources & evidence

ORD record: ord-c946161eab3948f7b640eab25889de5b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000010B2

Reaction notes

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