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

HRID 1417824Notes

Reaction equation

HRID 1417824 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-00c4dcd48dcc45d8b88d6ea5a27e4f0c
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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