HCID 86590594, compound → HCID 58800323, compound

HRID 347389Notes

Reaction equation

HRID 347389 reaction equation
C(O[CH2:10][C@H:11]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1)[CH2:12][CH:13]=[O:14])(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[N:21]1([C:18]2[CH:19]=[CH:20][C:15]([C@H:11]([CH3:10])[CH2:12][CH:13]=[O:14])=[CH:16][CH:17]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 1

HCID 86590594HCID 86590594, compound

Product 1

HCID 58800323HCID 58800323, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution (R)-3-(4-pyrolidin-1-yl-phenyl)-butyraldehyde (201 mg, 0.923 mmol, 1.00 equiv) in CH2Cl2 (0.5 mL) was added to a stirring solution of sodium borohydride (37.1 mg, 1.00 mmol, 1.08 equiv) in ethanol (3.0 mL). After 5 min, the reaction was diluted with saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (30 mL). The organic layer was separated and washed with saturated solutions of NaHCO3 and NaCl. The resulting solution was then dried over Na2SO4 and concentrated in vacuo. The residual oil (201 mg, 0.915 mmol, 1.00 equiv) was exposed to tert-butyldimethylsilyl chloride (276 mg, 1.83 mmol, 2.00 equiv), triethylamine (0.28 mL, 2.0 mmol, 2.2 equiv), and DMAP (10 mg) in CH2Cl2 (1.5 mL). After one hour, the reaction mixture was subjected directly to silica gel chromatography. Elution with 10% Et2O in hexanes followed by concentration of two fractions in vacuo afforded 35 mg of S3 as a colorless oil (0.10 mmol, 11% yield) that was spectroscopically identical in all respects to (S)-4-benzoyloxy-3-(4-pyrolidin-1-yl-phenyl)-butyraldehyde. [α]D (reference)=−28.7 (c=1.20, CHCl3); [α]D (observed)=−34.8 (c=0.994, CHCl3).

Sources & evidence

ORD record
ord-ff9ec3c8309c440eaeaeb2bb6487e53f
Source dataset
uspto-grants-2007_02
Patent number
US07173139B2

Reaction notes

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