2-Amino-6-chlorobenzaldehyde → (+/-)-(2-Amino-6-chlorophenyl)-cyclopentyl-methanol

HRID 2117279

Reaction equation

HRID 2117279 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[O:5].[CH:11]1([Mg]Br)[CH2:15][CH2:14][CH2:13][CH2:12]1>C(OCC)(=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[OH:5]

Participants

4

Reactant 2

HCID 223995122-Amino-6-chlorobenzaldehydeHCID 178419650HCID 178419650, compound

Product 1

HCID 69315836(+/-)-(2-Amino-6-chlorophenyl)-cyclopentyl-methanolYield 36%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared using General Method 1 (EXAMPLE 1) from 2-amino-6-chlorobenzaldehyde (0.30 g, 1.9 mmol) and cyclopentylmagnesium bromide (2 M in ether, 1.9 mL)) to afford 0.16 g (36%) of (±)-(2-amino-6-chlorophenyl)-cyclopentyl-methanol after flash chromatography (4:1 hexanes:ethyl acetate).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-ada438d7963c4adbb6c39fe67aac7a39
Source dataset
uspto-grants-2008_10
Patent number
US07442696B2

Linked notes

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