Triethylamine → benzyl (3S)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 515881Notes

Reaction equation

HRID 515881 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([CH2:11][OH:12])[NH:2]1.Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C(N(CC)CC)C>ClCCl>[OH:12][CH2:11][C@@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1][N:2]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 776757[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol

Product 1

HCID 12114557benzyl (3S)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is obtained using a protocol from the literature (R. B. Kawthekar et al South Africa Journal of Chemistry 63, 195, 2009) starting from 15 g of (3S)-1,2,3,4-tetrahydroisoquinolin-3-ylmethanol (91.9 mmol) in the presence of benzyl chloroformate and triethylamine in solution in dichloromethane. After purification by chromatography over silica gel using petroleum ether and ethyl acetate as eluants, the title product is obtained in the form of an oil.

Workup

  1. customThis compound is obtained
  2. customAfter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-216b40146f6640aa91eaefab917d1404
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

Loading…