Methanol → 2-[(-)-Isochroman-1-yl]-(+/-)-1-methylethylamine

HRID 368843Notes

Reaction equation

HRID 368843 reaction equation
[CH:1]1([CH2:11][C:12](=O)[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.C([O-])(=O)C.[NH4+].CO.C([BH3-])#[N:23].[Na+]>C(O)(=O)C.C1COCC1>[CH:1]1([CH2:11][CH:12]([NH2:23])[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1

Participants

7

Reactant 4

HCID 887MethanolHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 127770631-(Isochroman-1-yl)propan-2-one

Product 1

HCID 232888322-[(-)-Isochroman-1-yl]-(+/-)-1-methylethylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (-)-(isochroman-1-yl)acetone (LXXXIV, 0.73 g), ammonium acetate (1.48 g), methanol (2.5 ml), and THF (2.5 ml) is stirred for 25 min and then acetic acid (1.5 ml) and sodium cyanoborohydride (0.48 g) are added. After stirring for 2 hr, the mixture is concentrated and the residue is stirred with dichloromethane and sodium hydroxide (4N). The mixture is extracted with dichloromethane and washed with saline/sodium hydroxide (1N). The organic phase is separated and dried over sodium sulfate to give 2-[(-)-isochroman-1-yl]-(±)-1-methylethylamine.

Workup

  1. stirringAfter stirring for 2 hr
  2. concentrationthe mixture is concentrated
  3. stirringthe residue is stirred with dichloromethane and sodium hydroxide (4N)
  4. extractionThe mixture is extracted with dichloromethane
  5. washwashed with saline/sodium hydroxide (1N)
  6. customThe organic phase is separated
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-0e687e9706ef40f6b1a61dab25d6fcb1
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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