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

HRID 1672663Notes

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 of a 1 M borane-THF complex solution (47.73 mmol) are added dropwise to a solution of 8 g (23.71 mmol) of methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate from Example 72A in 200 ml of THF at −10° C. After warming to −5° C., the mixture is stirred at this temperature for 4 hours. After reaction is complete, the reaction mixture is mixed with saturated sodium bicarbonate solution, and the solvent is concentrated to dryness. The residue is taken up in dichloromethane, dried over sodium sulfate and 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% yield) of a colorless solid are obtained.

Workup

customAfter reaction
concentrationthe solvent is concentrated to dryness
dry with materialdried over sodium sulfate
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% yield) of a colorless solid are obtained

Sources & evidence

ORD record: ord-a64f1a0e88434f2cb4f45d7ac17dd10e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998988B2

Reaction notes

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