Butanal → HCID 54564421, compound

HRID 2290165Notes

Reaction equation

HRID 2290165 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17]([CH3:22])([CH3:21])[O:16][C:15]3([CH3:24])[CH3:23])=[CH:7][CH:6]=1)[CH3:2].C([BH3-])#N.[Na+].[CH:30](=O)[CH2:31][CH2:32][CH3:33]>C(O)(=O)C.O1CCCC1>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:30][CH2:31][CH2:32][CH3:33])[C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17]([CH3:22])([CH3:21])[O:16][C:15]3([CH3:24])[CH3:23])=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 3

HCID 261ButanalHCID 5003444Sodium cyanoborohydrideHCID 15454095HCID 15454095, compound2×

Product 1

HCID 54564421HCID 54564421, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure Q and using 4-[(1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 79, 0.2 g, 0.64 mmol), sodiumcyanoborohydride (0.121 g, 1.92 mmol) and butyraldehyde (1 mL, 11.09 mmol) in 5 mL of acetic acid and 5 mL of tetrahydrofuran, the title compound (0.21 g, 88%) was obtained as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.86 (d, 2H, J=9.1 Hz), 7.11 (d, 1H, J=8.7 Hz), 7.07 (d, 1H, J=8.1 Hz), 6.90 (s, 1H), 6.68 (d, 2H, J=8.9 Hz), 4.32 (q, 2H, J=7.1 Hz), 3.70 (t, 2H, J=7.8 Hz), 1.74-1.62 (m, 2H) 1.55 (s, 6H), 1.51 (s, 6H), 1.45-1.33 (m, 2H), 1.35 (t, 3H, J=7.1 Hz), 0.95 (t, 3H, J=7.4 Hz).

Sources & evidence

ORD record
ord-d890bfd3e97043cea8c77329731fe688
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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