Sodium Hydroxide → 3-Methoxymethylamino-1-(2-thienyl)propan-1-ol

HRID 1171924Notes

Reaction equation

HRID 1171924 reaction equation
Cl.[CH3:2][O:3][CH2:4][NH:5][CH2:6][CH2:7][C:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)=[O:9].[OH-].[Na+].[BH4-].[Na+]>CO.O>[CH3:2][O:3][CH2:4][NH:5][CH2:6][CH2:7][CH:8]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[OH:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 667695353-Methoxymethylamino-1-(2-thienyl)-1-propanone hydrochloride salt

Product 1

HCID 687698733-Methoxymethylamino-1-(2-thienyl)propan-1-olYield 102.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

38.6 g of 3-methoxymethylamino-1-(2-thienyl)-1-propanone hydrochloride salt obtained in Step 1 was dissolved in 115 g of methanol and 40 g of water. The pH value of the resulting solution was adjusted to 11 by addition of 45% NaOH. 2.5 g of sodium borohydride was added, and the mixture was stirred for 1 hour. Afterward the reaction mixture was filtered, concentrated and extracted with 80 g of toluene. The organic layer was concentrated to obtain 33.8 g of 3-methoxymethylamino-1-(2-thienyl)propan-1-ol as an oily product. 1H NMR (400 MHz, CDCl3) δ (ppm)=3.0 (s, 3H), 3.0-3.1 (m, 1H), 4.1 (s, 3H), 4.0-4.1 (m, 3H), 6.1 (dt, J=7.4, 15.4 Hz, 1H), 6.9 (d, J=15.7 Hz, 1H), 7.0 (dd, J=3.7, 5.0 Hz, 1H), 7.1 (d, J=3.4 Hz, 1H).

Workup

  1. filtrationAfterward the reaction mixture was filtered
  2. concentrationconcentrated
  3. extractionextracted with 80 g of toluene
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-da6773cc6ac64313bc03978d4e07ea82
Source dataset
uspto-grants-2010_11
Patent number
US07829731B2

Reaction notes

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