Benzaldehyde → HCID 73554247, compound

HRID 1614706Notes

Reaction equation

[ClH:1].[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[OH-].[Na+].[Na+].[Cl-].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>CO>[ClH:1].[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 4 °C

Procedure

A solution of 20 g (0.129 mol) L-serine methyl ester hydrochloride (XXIV) in 100 mL MeOH was adjusted to pH 8 with 12.9 mL 10M NaOH thus precipitating NaCl. Benzaldehyde (15.0 g, 0.141 mol) was added and stirred well for 30 min. After cooling to 4° C., 2.43 g (0.064 mol) NaBH4 was added in parts over one hour. The reaction was then warmed to ambient temperature and stirred for another hour. Analysis by ion pair HPLC showed that aside from the desired product, identified by co-elution with material obtained by esterification of N-benzyl-L-serine, the only other product observed was benzyl alcohol. The reaction was filtered, concentrated, and dried. The thick residue was dissolved in 120 mL acetone, refiltered to remove more salt, adjusted to between pH 1 to 1.5 with HCL gas, 750 mL Et2O added, product collected by centrifugation, and dried, giving 28.1 g colorless hygroscopic solid. Chromatographic comparison to purified material showed this to contain 91.6 mmol (71%). MS (E.I., direct insertion) m/z(% relative abundance) 210(MH+)(5), 178(55), 150(64), 118(6), 106(29), 91(100); HRMS (+DCI, CH4) m/z calcd for C11H16NO3 (MH+) 210.113, found 210.112.

Workup

temperatureThe reaction was then warmed to ambient temperature
stirringstirred for another hour

Sources & evidence

ORD record: ord-db72b7f1f4e04c97806b4467c42e8ed1
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05198547

Reaction notes

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