Triethylamine → Methyl 2-{[4-(2-tert-butoxy-1,1-dimethyl-2-oxoethoxy)benzyl]amino}butyrate

HRID 353168Notes

Reaction equation

HRID 353168 reaction equation
[CH:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]([CH3:17])([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[NH2:20][CH:21]([CH2:25][CH3:26])[C:22]([O-:24])=[O:23].[CH2:27](N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:12]([O:11][C:9](=[O:10])[C:8]([CH3:17])([CH3:16])[O:7][C:6]1[CH:18]=[CH:19][C:3]([CH2:1][NH:20][CH:21]([CH2:25][CH3:26])[C:22]([O:24][CH3:27])=[O:23])=[CH:4][CH:5]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 21889526Alpha-aminobutyrate2×HCID 22708193tert-Butyl 2-(4-formylphenoxy)-2-methylpropanoate

Product 1

HCID 22708231Methyl 2-{[4-(2-tert-butoxy-1,1-dimethyl-2-oxoethoxy)benzyl]amino}butyrateYield 89%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

Similarly to the procedure of Example I-5, 1.20 g (4.54 mmol) of tert-butyl 2-(4-formylphenoxy)-2-methylpropionate (Example I-4) and 0.70 g (4.54 mmol) of methyl DL-2-aminobutyrate are reacted at room temperature with 0.92 g (9.08 mmol) of triethylamine and 1.44 g (6.81 mmol) of sodium triacetoxyborohydride in 10 ml of dichloroethane. A further 0.9 g (4.25 mmol) of sodium triacetoxyborohydride and 0.35 g (2.27 mmol) of methyl DL-2-aminobutyrate are added and the mixture is heated at 40° C. for 3 h, giving 1.47 g (89%) of methyl 2-{[4-(2-tert-butoxy-1,1-dimethyl-2-oxoethoxy)benzyl]amino}butyrate.

Sources & evidence

ORD record
ord-17eff5b5aead423fb02c1818a0dd98d7
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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