Red-Al → HCID 178484806, compound

Temperature

105 °C

Vitride solution (65%, 767 ml, 2.465 mol) was added dropwise over 1 h to a solution of trans-4-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (commercially available, 100 g, 0.4109 mol) in toluene (1 l). After the addition was complete the reaction mixture was heated to reflux for 100-110° C. The reaction mixture was quenched with aq. Sodium sulphate solution (800 ml) at temperatures below 10° C. The reaction mixture was filtered through celite and the filter cake washed with DCM (500 ml) followed by water (100 ml). The organics layer was separated and the aqueous layer extracted twice with DCM (600 ml then 400 ml). The combined organics layers were dried over sodium sulphate and concentrated in vacuo to give the title compound (62 g).

1. additionAfter the addition
2. temperaturewas heated
3. customThe reaction mixture was quenched with aq. Sodium sulphate solution (800 ml) at temperatures below 10° C
4. filtrationThe reaction mixture was filtered through celite
5. washthe filter cake washed with DCM (500 ml)
6. customThe organics layer was separated
7. extractionthe aqueous layer extracted twice with DCM (600 ml
8. dry with materialThe combined organics layers were dried over sodium sulphate
9. concentrationconcentrated in vacuo

ORD record

ord-11cf871695774a8b9f323026dfcf4a77

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09161939B2