Methanol → (R)-norfluoxetine (D)-tartrate

HRID 1797223Notes

Reaction equation

HRID 1797223 reaction equation
[C:1]([C@H:4]([C@@H:6]([C:8]([O-:10])=[O:9])[OH:7])[OH:5])([O-:3])=[O:2].C[NH:12][CH2:13][CH2:14][C@@H:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>CC(OC)(C)C>[CH:19]1[CH:20]=[CH:21][C:16]([C@H:15]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=2)[CH2:14][CH2:13][NH2:12])=[CH:17][CH:18]=1.[C:1]([C@H:4]([C@@H:6]([C:8]([O-:10])=[O:9])[OH:7])[OH:5])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 1548970(+)-FluoxetineHCID 5460284D-Tartrate

Product 1

HCID 86759990(R)-norfluoxetine (D)-tartrate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

(D)-Tartrate (10): To a 50 mL round bottom flask was added 1.63 g (5.53 mmol) of (R)-fluoxetine free amine (9). To this was added 20 mL of methanol and the amine was dissolved. To this solution was added 840 mg of (D)-tartaric acid (5.6 mmol). The reaction mixture was stirred for 30 minutes and then methanol was rotoevaporated to dryness. The solid was slurred in 20 mL of TBME and filtered. The white solid was dried in a vacuum oven for 5 hours at ˜40° C. 2.08 g of (R)-norfluoxetine (D)-tartrate was obtained (85%). 99.44% ee, 99.53 A % purity. 1H NMR ppm (δ), DMSO 7.63–7.10 (m, 9H), 5.61 (m, 1H, CH—O), 3.90 (dd, 2H), 2.90 (m, 2H), 2.50 (s, 1H), 2.35–2.08 (m, 2H). 13C NMR ppm (δ), DMSO 175.3, 160.8, 140.8, 129.5, 128.71, 127.5, 126.6, 117.0, 77.0, 72.3, 36.4.

Workup

  1. filtrationfiltered
  2. customThe white solid was dried in a vacuum oven for 5 hours at ˜40° C

Sources & evidence

ORD record
ord-cb252aa7ac904abdb12d58eb8063ab29
Source dataset
uspto-grants-2006_04
Patent number
US07034059B2

Reaction notes

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