Formaldehyde → HCID 69321373, compound

HRID 1350143Notes

Reaction equation

HRID 1350143 reaction equation
[CH2:1]([C@@H:3]1[CH2:24][O:23][C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[NH:4]1)[N:11]=[C:10]([O:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:8]3[C:19]([F:22])([F:21])[F:20])[CH3:2].C=O.[BH3-][C:28]#N.[Na+]>C(O)(=O)C>[CH2:1]([C@@H:3]1[CH2:24][O:23][C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[N:4]1[CH3:28])[N:11]=[C:10]([O:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:8]3[C:19]([F:21])([F:22])[F:20])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69319657HCID 69319657, compound

Product 1

HCID 69321373HCID 69321373, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

This compound was prepared by General Method 5 (EXAMPLE 1) from (3R)-3-ethyl-3,4-dihydro-8-isopropoxy-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline (0.015 g, 0.044 mmol), paraformaldehyde (0.013 g, 0.44 mmol) and NaCNBH3 (0.014 g, 0.22 mmol) in 1 mL glacial acetic acid to afford 0.014 g (93%) of (3R)-3-ethyl-3,4-dihydro-8-isopropoxy-4-methyl-10-(trifluoromethyl)-2H-[1,4]oxazino[2,3-f]quinoline, of sufficient purity as to be used directly in the next reaction. Rf0.5 (9:1 hexane:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, 1H, J=9.0), 7.20 (d, 1H, J=9.0), 7.18 (s, 1H), 5.48 (septet, 1H, J=6.2), 4.29 (dd, ABX, 1H, J=10.7, 2.5), 4.02 (dd, ABX, 1H, J=10.7, 2.7), 3.21–3.16 (m, 1H), 3.03 (s, 3H), 1.74–1.56 (m, 2H), 1.39 (d, 3H, J=6.2), 1.37 (d, 3H, J=6.2), 0.99 (t, 3H, J=7.5).

Sources & evidence

ORD record
ord-1471dac3cac7436db2e5978a44109a7c
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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