Acetone Cyanohydrin → HCID 68968606, compound

HRID 1726244Notes

Reaction equation

HRID 1726244 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14](O)[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)(O)[C:28]#[N:29].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:28]#[N:29])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68970431HCID 68970431, compound

Product 1

HCID 68968606HCID 68968606, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[hydroxy-(4-trifluoromethyl-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (990 mg, 2.75 mmol), acetone cyanohydrin (913 mg, 10.73 mmol) and Ph3P (2.5 g, 9.63 mmol) in THF (25 mL) was added DIAD (2.2 g, 10.94 mmol) in THF (10 mL) over 5 hours at 0° C. and the resulting mixture was stirred for another 72 hours at room temperature. Standard work-up and purification afforded 4-[cyano-(4-trifluoromethyl-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (539 mg, 53%) as a white foam.

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-484284a172844f618cb88a6c1bcd0fc6
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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