4-Pyridinecarboxaldehyde → HCID 57151801, compound

HRID 841941Notes

Reaction equation

[O:1]([CH2:8][C@H:9]1[NH:13][CH2:12][C@H:11]([OH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]1[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1>>[O:1]([CH2:8][C@H:9]1[N:13]([CH2:21][C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)[CH2:12][C@H:11]([OH:14])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 133894-Pyridinecarboxaldehyde

HCID 57243395HCID 57243395, compound

Product 1

HCID 57151801HCID 57151801, compound

Procedure

The title compound was prepared by a similar method to Preparation 35 from (3R,5S)-5-(phenoxymethyl)pyrrolidine-3-ol [see Preparation 37] and 4-pyridinecarboxaldehyde. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 95:5, by volume, chloroform:methanol to afford (3R,5S)-5-(phenoxymethyl)-1-(4-pyridinylmethyl)pyrrolidine-3-ol as a white solid.

Workup

customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 95:5, by volume, chloroform

Sources & evidence

ORD record: ord-88666ee941724898a7a0f17e3d93571a
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372736B1

Reaction notes

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