Cyclohexanecarboxaldehyde → methyl (2RS,3SR)-3-cyclohexyl-3-hydroxy-2-(2-methoxyphenylmethyl)propionate

HRID 1533259Notes

Reaction equation

HRID 1533259 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[CH:15]1([CH:21]=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:15]1([CH:21]([OH:22])[CH:10]([CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:11]([O:13][CH3:14])=[O:12])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 562482Methyl 3-(2-methoxyphenyl)propanoate

Product 1

HCID 86756557methyl (2RS,3SR)-3-cyclohexyl-3-hydroxy-2-(2-methoxyphenylmethyl)propionate

Procedure

Methyl 3-(2-methoxyphenyl)propionate (1.80 g) was reacted with cyclohexane carbaldehyde (1.25 g) in substantially the same manner as that of Preparation 1-4) to give less polar isomer of methyl (2RS,3SR)-3-cyclohexyl-3-hydroxy-2-(2-methoxyphenylmethyl)propionate (isomer A) (0.706 g) and more polar isomer of (2RS,3RS)-isomer of the same (isomer B) (0.940 g).

Workup

  1. customof Preparation 1-4)

Sources & evidence

ORD record
ord-b579cc72c7254289bcada1ed93f3570d
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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