Borane;tetrahydrofuran → HCID 22099009, compound

HRID 2393802Notes

Reaction equation

HRID 2393802 reaction equation
[O:1]=[C:2]([CH2:9][C:10](=[O:13])[C:11]#[CH:12])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].B.C1COCC1.C1C2C(=CC=CC=2)C=CC=1CN1CCC[C@H]1CO>C1COCC1.CO>[OH:1][CH:2]([CH2:9][CH:10]([OH:13])[C:11]#[CH:12])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 22098985HCID 22098985, compoundHCID 22876508HCID 22876508, compound

Product 1

HCID 22099009HCID 22099009, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 mg (0.27 mmol) of ethyl 3,5-dioxo-6-heptynoate was dissolved in 5 ml of THF and 52 ml of methanol. Then, with or without addition of aluminum tri-i-propoxide as a metal reagent, a reaction was conducted at 20° C. for 20 hours using 5.4 ml of a 1.0M BH3.THF solution and 6.2 mg (0.027 mmol) of the (S)-N-(β-naphthyl)methyl-2-pyrrolidine methanol (compound (S)-II-1) obtained in Example 1, to obtain ethyl 3,5-dihydroxy-6-heptynoate (VI-2) as oily desired product.

Workup

  1. customobtained in Example 1

Sources & evidence

ORD record
ord-dd1172e898a0416f92a4e619e8082f86
Source dataset
uspto-grants-1998_09
Patent number
US05808098

Reaction notes

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