Water → HCID 59277619, compound

HRID 2097122Notes

Reaction equation

HRID 2097122 reaction equation
[C:1]([C:5]1[C:6]([O:13][CH2:14][CH2:15][CH3:16])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:17][NH2:18].[BH4-].[Na+].O>CO>[C:1]([C:5]1[C:6]([O:13][CH2:14][CH2:15][CH3:16])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH:18][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 59277541HCID 59277541, compound

Product 1

HCID 59277619HCID 59277619, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-tert-Butyl-2-propoxy-benzaldehyde (1.15 g, 5.21 mmol) was dissolved in anhydrous methanol (25 ml). Methylamine (2.00 ml of 33% solution in ethanol, 16.1 mmol) was added and the reaction was stirred for 3 h. The solution was concentrated to a yellow oil and then dissolved in anhydrous methanol (25 ml). Sodium borohydride (198 mg, 5.23 mmol) was added and the mixture was stirred overnight at room temperature. Water (10 ml) was added and the solution was concentrated. Sodium hydroxide (30 ml, 1N) was added and the aqueous layer was extracted with ethyl acetate (3×50 ml). Combined organic layers were dried over MgSO4, filtered and concentrated to afford (3-tert-butyl-2-propoxy-benzyl)-methyl-amine (1.18 g, 96%) as a clear oil: 1H NMR (400 MHz, DMSO-d6) δ 7.28 (d, J=8.0 Hz, 1H), 7.15 (d, J=8.0 Hz, 1H), 6.97 (y J=8.0, y1H), 3.79 (t, J=4.0 Hz, 2H), 3.61 (s, 2H), 2.28 (s, 3H), 1.80-1.75 (m, 2H), 1.33 (s, 9H), 1.03 (t, J=8.0 Hz, 3H).

Workup

  1. concentrationThe solution was concentrated to a yellow oil
  2. dissolutiondissolved in anhydrous methanol (25 ml)
  3. stirringthe mixture was stirred overnight at room temperature
  4. concentrationthe solution was concentrated
  5. additionSodium hydroxide (30 ml, 1N) was added
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×50 ml)
  7. dry with materialCombined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7d7aee6d313b4852a5e74820a1f33e1d
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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