Isobutyraldehyde → HCID 57687748, compound

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:15])[CH2:13][OH:14])([CH3:4])([CH3:3])[CH3:2].[CH:17](=O)[CH:18]([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:15][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:13][OH:14])([CH3:4])([CH3:2])[CH3:3]

Participants

Procedure

(S)-(5-Amino-6-hydroxy-hexyl)-carbamic acid tert-butyl ester (3) (6.85 g) was dissolved in 200 mL CH2Cl2. Isobutyraldehyde (2.67 mL) was added and this solution was stirred for 2 hours. Sodium triacetoxyborohydride (1.1 eq) was added and the solution was stirred for 2 hours at RT. The solution was washed with sat. NaHCO3. The milky organic phase was separated and evaporated to dryness. The residue was purified by column chromatography using 99:1 EtOAc (100%) to EtOAc-MeOH(NH3) 99-1. as the eluent. Fractions containing the product were evaporated yielding 2.60 g (31%) of the title compound.