Pivalaldehyde → HCID 59290437, compound

Sodium triacetoxyborohydride (5.30 g) was added to a cooled at 0° C. solution of aminoacetaldehyde diethyl acetal (2.91 mL) and pivalaldehyde (2.21 mL) in dichloromethane (50 mL). The reaction was stirred for 16 h, allowing the temperature to warm to ambient conditions. Water (50 mL) was added, followed by portionwise addition of sodium bicarbonate (8.40 g), causing effervescence. The mixture was stirred vigorously for 1 h, then allowed to partition. The phases were then separated and the aqueous phase extracted with further dichloromethane (20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford N-(2,2-diethoxyethyl)-2,2-dimethylpropan-1-amine (3.79 g) as an oil. 1H NMR (400 MHz, CDCl3) δ 4.63 (t, J=5.6 Hz, 1H), 3.71 (dq, J=9.5, 7.1 Hz, 2H), 3.55 (dq, J=9.4, 7.1 Hz, 2H), 2.73 (d, J=5.6 Hz, 2H), 2.37 (s, 2H), 1.22 (t, J=7.1 Hz, 6H), 0.91 (s, 9H)

1. temperatureto warm to ambient conditions
2. stirringThe mixture was stirred vigorously for 1 h
3. customto partition
4. customThe phases were then separated
5. extractionthe aqueous phase extracted with further dichloromethane (20 mL)
6. dry with materialThe combined organic extracts were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-d2b4b3fbe2054ee990c95b76139dd705

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017602B2