Isobutyraldehyde → HCID 18418694, compound

HRID 990400Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:17])[CH2:14][NH:15][CH3:16])=[CH:4][CH:3]=1.[CH:25](=O)[CH:26]([CH3:28])[CH3:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:17])[CH2:14][N:15]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH3:16])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-[4,4-Bis-(4-fluoro-phenyl)-butyl]-2-methylamino-acetamide (157 mg, 0.47 mmol) was dissolved in CH2Cl2 (5 mL), treated with isobutyraldehyde (43 mL, 0.47 mmol), stirred for 30 minutes, then cooled to 0° C., treated with NaBH(OAc)3 (150 mg, 0.71 mmol), and stirred overnight at room temperature. The reaction was diluted with EtOAc (100 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2 to give 168 mg (92%) of the desired product as a sticky solid. MS: 389.3 (M+1 for C23H30N2O1F2); sticky solid; TLC (SiO2), Rf 0.44 (6% MeOH/CH2Cl2); HPLC (7:3 CH3CN/H2O with 0.1% TFA, C-18 column) 100%, RT=2.067 min.

Workup

stirringstirred overnight at room temperature
washwashed with saturated bicarbonate solution and brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-de93add33f8140d8bc28d1dfe20b1c12
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458781B1

Reaction notes

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