Potassium;tri(butan-2-yl)boranuide → HCID 11171416, compound

HRID 842442Notes

Reaction equation

HRID 842442 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][C@H:3]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].CCC(C)[BH-](C(C)CC)C(C)CC.[K+]>C1COCC1>[OH:8][C@@H:5]1[CH2:4][C@@H:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C@H:2]([CH3:1])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 11206192HCID 11206192, compound

Product 1

HCID 11171416HCID 11171416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

reacting said ethyl (1R,2R)-2-methylcyclohexane-5-one-1-carboxylate (11) with K-Selectride (potassium tri-sec-butylborohydride) in THF at −78° C. to produce ethyl (1R,2R,5S)-5-hydroxy-2-methylcyclohexane-1-carboxylate (12), and

Workup

  1. customat −78° C.

Sources & evidence

ORD record
ord-65eb2bb484354cc0972691ebf2eee7b6
Source dataset
uspto-grants-2002_04
Patent number
US06375943B1

Reaction notes

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