(-)-Mandelic acid → (-)-7-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane d-mandelate

HRID 389251Notes

Reaction equation

HRID 389251 reaction equation
[NH2:1][C:2]1([CH3:16])[C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1.[C:17]([OH:27])(=[O:26])[C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[OH:19]>C1(C)C=CC=CC=1>[C:17]([OH:27])(=[O:26])[C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[OH:19].[NH2:1][C:2]1([CH3:16])[C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 11914(-)-Mandelic acidHCID 249623127-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane

Product 1

HCID 131728788(-)-7-Amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane d-mandelate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Toluene (11.5 L) was added to a solution (1,660 mL) of 7-amino-5-benzyl-7-methyl-5-azaspiro[2.4]heptane (2,202 g, purity: 35%) in toluene, and D-mandelic acid (325.2 g) was added to the mixture, followed by cooling. Seed crystals for the title compound were added to the cooled mixture, followed by stirring overnight at an internal temperature of −10° C. The precipitated crystals were collected through filtration and washed twice with cold toluene, followed by drying under reduced pressure. The thus-obtained crude products (first crude crystals) were suspended under stirring in toluene (2.2 L) at room temperature. After 2.5 hours, the suspension was filtered so as to collect crystals. The collected crystals were washed with cold toluene, followed by drying under reduced pressure, to thereby yield the title product as white crystals (first crystals) (365.4 g, yield: 27.1%, optical purity: 97.4% e.e.).

Workup

  1. additionwas added to the mixture
  2. temperatureby cooling

Sources & evidence

ORD record
ord-3bd331fb24ac4cde95d343d2f1c3f72a
Source dataset
uspto-grants-2013_02
Patent number
US08378119B2

Reaction notes

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