Benzaldehyde → (R)-methyl 2-(benzylamino)-3-phenylpropanoate

HRID 1040281Notes

Reaction equation

HRID 1040281 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH2:21]([NH:6][C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([O:3][CH3:2])=[O:14])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

Product 1

HCID 13388971(R)-methyl 2-(benzylamino)-3-phenylpropanoateYield 72.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using D-phenylalanine methyl ester hydrochloride (2 gm, 9.2 mmol), THF (25 mL), MgSO4 (1.87 gm, 15.6 mmol), benzaldehyde (1.88 mL, 18.5 mmol), Et3N (1.28 mL, 9.2 mmol), sodium borohydride (699 mg, 18.5 mmol), and methanol (30 mL) to give 11g (1.8 gm, 72%) in FIG. 2. 1H NMR (500 MHz, CD3OD): δ 2.96 (2H, d, J=6.59 Hz), 3.53 (1H, t, J=7.08 Hz), 3.6 (3H, s), 3.63 (1H, d, J=12.93 Hz), 3.77 (1H, d, J=12.93 Hz), 7.13-7.18 (2H, m), 7.19-7.32 (8H, m). ESI-MS: 292.2 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-efc86669632a443691cde596162ae3c9
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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