Sodium Bicarbonate → Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[C:10](O)=[O:11])[CH3:2].C(=O)(O)[O-].[Na+]>C1COCC1>[C:21]([C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH:9]([CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])=[CH:20][CH:19]=1)#[N:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
54.19 ml of a 1 M borane-THF complex solution (54.19 mmol) are added dropwise to a solution of 8.6 g (27.1 mmol) of 2-[2-(4-cyanophenyl)ethyl]heptanedioic acid 7-ethyl ester from Example 84A in 200 ml of THF at −10° C. After warming to 0° C., the mixture is stirred at this temperature for 2 hours. After reaction is complete, saturated sodium bicarbonate solution is added to the reaction mixture, 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→1:4). 5.1 g (97% purity, 60% 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→1:4)
- custom5.1 g (97% purity, 60% yield) of a colorless solid are obtained
Sources & evidence
- ORD record
- ord-ddc6fa0f01aa4405b6fa46442f641333
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998988B2
Reaction notes
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