Sodium borohydride → HCID 11323609, compound

HRID 505365Notes

Reaction equation

HRID 505365 reaction equation
[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:4]=1[CH:5]=[N:6][CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10].[BH4-].[Na+].COC1C=C(C=CC=1OC)CNCC(OC)OC>C(O)C>[CH3:1][O:2][C:3]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:4]=1[CH2:5][NH:6][CH2:7][CH:8]([O:9][CH3:10])[O:11][CH3:12]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11448955HCID 11448955, compoundHCID 12378777HCID 12378777, compound

Product 1

HCID 11323609HCID 11323609, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Imine 11e (14.28 g, 0.05040 mol) was dissolved in ethanol (100 mL) and reacted with NaBH4 (3.00 g, 0.0793 mol) as described previously for compound 12a. A colorless oil (14.38 g, 100%) was obtained. 1H NMR (300 MHz, CDCl3) δ 6.89 (d, J=8.4 Hz, 1H), 6.57 (d, J=8.4 Hz, 1H), 4.45 (t, J=5.4 Hz, 1H), 3.87 (s, 3H), 3.82 (s, 3H), 3.80 (s, 2H), 3.70 (s, 3H), 3.31 (s, 6H), 2.68 (d, J=5.4 Hz, 2H); low resolution ESIMS m/z (rel intensity) 286 (MH+, 100), 181 (69). Anal. Calcd for C14H23NO5: C, 58.93; H, 8.12; N, 4.91. Found: C, 59.16; H, 8.24; N, 4.64.

Sources & evidence

ORD record
ord-34efab6fe6984226940861bc3317c2e0
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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