L-Tartaric acid → methyl (2S)-1-[(1S)-1-phenylethyl]azetidine-2-carboxylate

HRID 1953172Notes

Reaction equation

HRID 1953172 reaction equation
[CH3:1][C@H:2]([N:9]1[CH2:12][CH2:11][CH:10]1[C:13]([O:15][CH3:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>C(OC)(C)(C)C.CO>[C:17]([OH:26])(=[O:25])[CH:18]([CH:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19].[CH3:1][C@H:2]([N:9]1[CH2:12][CH2:11][C@H:10]1[C:13]([O:15][CH3:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 444305L-Tartaric acidHCID 15370446HCID 15370446, compound

Product 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 10998528methyl (2S)-1-[(1S)-1-phenylethyl]azetidine-2-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
29 °C

Procedure

A solution of methyl N-[(S)-methylbenzyl]azetidine-2-carboxylate (29.91 g, the ratio: 2S isomer/2R isomer=52/48) in methyl tert-butyl ether was added dropwise to a solution of L-tartaric acid (16.55 g) in methanol (20.26 g) under reflux. Further, 21.43 g of methanol was added and the obtained homogeneous solution was cooled to 29° C. A small amount of the crystals obtained in Example 6 was fed as seed crystals to initiate crystallization. Then, after cooled to 5° C., crystals were collected by filtration, washed with methyl tert-butyl ether and dried in vacuo to give tartaric acid salt of methyl N-[(S)-methylbenzyl]azetidine-2-(S)-carboxylate (25.36 g, yield: 48%, 91% d.e.).

Workup

  1. temperatureunder reflux
  2. customcrystallization
  3. temperatureThen, after cooled to 5° C.
  4. filtrationcrystals were collected by filtration
  5. washwashed with methyl tert-butyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3a5932377f7f43ff80970b481896ca0f
Source dataset
uspto-grants-2000_09
Patent number
US06114543

Reaction notes

Loading…