Sodium Bicarbonate → Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate

HRID 1913784Notes

Reaction equation

[C:1]([CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(O)=[O:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH:4]([CH2:1][OH:2])[CH2:5][CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)=[CH:23][CH:22]=1)#[N:25]

Participants

Conditions

Temperature: -5 °C

Procedure

47.43 ml (47.43 mmol) of a 1 M borane-THF complex solution are added dropwise to a solution of 8 g (23.71 mmol) of methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate from Example 47A in 200 ml of THF at −10° C. After the mixture has warmed to −5° C. it is stirred at this temperature for 4 h. After the reaction is complete, the reaction mixture is mixed with saturated sodium bicarbonate solution and the solvent is evaporated to dryness. The residue is taken up in dichloromethane, dried over sodium sulphate and, after filtration, again freed of solvent. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10). 5.8 g (98% purity, 74% of theory) of a colourless solid are obtained.

Workup

customthe solvent is evaporated to dryness
dry with materialdried over sodium sulphate
filtrationafter filtration
customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: ethyl acetate/cyclohexane 1:10)
custom5.8 g (98% purity, 74% of theory) of a colourless solid are obtained

Sources & evidence

ORD record: ord-e85cf9f462104ced98911a8a24e5c065
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609727B2

Reaction notes

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