(-)-Mandelic acid → HCID 131730090, compound

HRID 1751956Notes

Reaction equation

[NH2:1][CH2:2][C:3]1([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH:8]2[CH:4]1[CH:5]=[C:6]([CH2:10][CH3:11])[CH2:7]2.[C:20]([OH:30])(=[O:29])[C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22]>C(#N)C>[C:20]([OH:30])(=[O:29])[C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22].[NH2:1][CH2:2][C@:3]1([CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:9][C@@H:8]2[C@H:4]1[CH:5]=[C:6]([CH2:10][CH3:11])[CH2:7]2

Participants

Conditions

Temperature: 40 °C

Procedure

Acetonitrile (4.7 L, 8.6 v/w) was added to tert-butyl [6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (627.0 g, net: 543.6 g, 2.05 mol, 85:15 diastereomeric mixture), and the mixture was stirred at 40° C. To the reaction solution, D-mandelic acid (116.3 g, 0.76 mmol, 0.37 eq.) was added, and the mixture was stirred at 40° C. for 1 hour and then allowed to cool slowly to 3° C. After stirring at 3° C. for 1 hour, the resulting crystal was collected by filtration. Then, the crystal was dried under reduced pressure under the condition of 40° C. to obtain tert-butyl [(1R,5S,6S)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate D-mandelate as a white powder (251.2 g, yield: 29.4%, 97.6% ee, 99.6% de).

Workup

stirringthe mixture was stirred at 40° C. for 1 hour
temperatureto cool slowly to 3° C
stirringAfter stirring at 3° C. for 1 hour
filtrationthe resulting crystal was collected by filtration
customThen, the crystal was dried under reduced pressure under the condition of 40° C.

Sources & evidence

ORD record: ord-52b304563512442b8cd2484eb29825f5
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162971B2

Reaction notes

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