Potassium tert-butoxide → (S)-3-methoxymethylamino-1-(2-thienyl)propan-1-ol

HRID 41608Notes

Reaction equation

HRID 41608 reaction equation
[CH3:1][O:2][CH2:3][NH:4][CH2:5][CH2:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8].CC(C)([O-])C.[K+].[H][H]>CO>[CH3:1][O:2][CH2:3][NH:4][CH2:5][CH2:6][C@@H:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[OH:8]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 66769536HCID 66769536, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66769498(S)-3-methoxymethylamino-1-(2-thienyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A degassed methanol solution (4 mL) containing RuCl2((R)-3,5-xylylBINAP)((2R)-DAIPEN) (10 mg), 3-methoxymethylamino-1-(2-thienyl)-1-propanone (160 mg), potassium tert-butoxide (100 mg) and methanol (10 mL) was charged in a glass autoclave under an argon gas flow. After deaeration and replacement by argon, hydrogen was introduced to a predetermined pressure. The resulting solution was hydrogenated at 20° C. for 12 hours. Upon completion of hydrogenation, the reaction mixture was concentrated to give an oily product (161 mg, 95.8% measured by HPLC assay, 95% ee).

Workup

  1. additionwas charged in a glass autoclave under an argon gas flow
  2. concentrationUpon completion of hydrogenation, the reaction mixture was concentrated
  3. customto give an oily product (161 mg, 95.8% measured by HPLC assay, 95% ee)

Sources & evidence

ORD record
ord-54bf1877baef44dd973d826292acd4a7
Source dataset
uspto-grants-2013_09
Patent number
US08530674B2

Reaction notes

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