Hydroxylamine → HCID 22625133, compound

HRID 279416Notes

Reaction equation

HRID 279416 reaction equation
NO.[CH3:3][C:4]([CH3:8])([CH3:7])[CH:5]=[O:6].C([Zn][CH2:12][CH3:13])C.[C:14](OC(=O)C)(=[O:16])[CH3:15]>CCCCCC.C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[C:14]([O:6][CH:5]([CH2:12][CH3:13])[C:4]([CH3:8])([CH3:7])[CH3:3])(=[O:16])[CH3:15]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 7918Acetic AnhydrideHCID 12417PivalaldehydeHCID 178418750HCID 178418750, compound

Product 1

HCID 22625133HCID 22625133, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 7964ChlorobenzeneSolventHCID 8058HexaneSolvent

Procedure

A vial was charged with aminoalcohol A (0.0061 g, 0.025 mmol) prepared as in Example 13. To the vial was added 1.63 mL of a stock solution containing trimethylacetaldehyde (0.26 g), chlorobenzene internal standard (0.26 g), 1 M diethylzinc in hexane (6.0 mL), and toluene (3.0 mL). After 48 h acetic anhydride (0.200 mL) was added. After an additional 72 h a sample of the solution was analyzed by gas chromatography at 70° C. on a Cyclodex B stationary phase. The product 3-acetoxy-2,2-dimethylpentane was formed in 57% yield and 97% enantiomeric excess. The identity and yield of the product was established by comparison with an authentic sample prepared by treatment of racemic 2,2-dimethyl-3-pentanol with acetic anhydride.

Workup

  1. customA (0.0061 g, 0.025 mmol) prepared as in Example 13

Sources & evidence

ORD record
ord-ad2eedc72b0048c68e39a937d16566ed
Source dataset
uspto-grants-2002_03
Patent number
US06362344B1

Reaction notes

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