Sodium Carbonate → HCID 43230241, compound

A suspension of DL-alanine methyl ester hydrochloride (41.8 g, 300 mmol) in dry dichloromethane (650 mL) was treated with potassium acetate (30.0 g, 306 mmol) and the reaction mixture stirred for ten minutes at rt. Reaction flask was then cooled to 10° C. and treated with 3-methylbutanal (25.8 g, 300 mmol). This was followed by the addition of sodium triacetoxyborohydride (82.5 g, 390 mmol) in portions over a period of ten minutes. Reaction mixture was stirred at room temperature for 16 h. Then saturated aqueous sodium bicarbonate solution was added to the reaction and the resulting mixture was stirred for another 30 minutes. The reaction mixture was then further basified with aqueous sodium carbonate to pH=˜10. Dichloromethane layer was separated and the aqueous layer extracted with dichloromethane (3×100 mL). Organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and evaporated to give titled product as a colorless oil (yield: 72%). 1HNMR (300 MHz, CDCl3): δ 0.92-0.98 (m, 6H), 1.28-1.41 (m, 5H), 2.48-2.68 (m, 3H), 3.30-3.40 (m, 1H), 3.74 (s, 3H).

1. customReaction flask
2. temperaturewas then cooled to 10° C.
3. customReaction mixture
4. stirringwas stirred at room temperature for 16 h
5. stirringthe resulting mixture was stirred for another 30 minutes
6. customDichloromethane layer was separated
7. extractionthe aqueous layer extracted with dichloromethane (3×100 mL)
8. washwashed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. customevaporated

ORD record

ord-09e13a5affc6434e83e058c5382909bc

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09351974B2