Tetrahydrofuran → HCID 10017724, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH2:19][CH3:20])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[AlH3].C1COCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH2:19][CH3:20])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
4
Procedure
The title compound of Example 15 (base) (6.39 g, 20.3 mmol) was reduced with a 1.0M solution of AlH3 in THF (60 mL, 60 mmol, 3 eq) as described in Example 8 to give the crude product as a colorless oil (6.1 g, quantitative). The oxalate salt (6.5 g, 80% ) crystallized from 2-propanol/MeOH (1:1): mp 181°-182° C. (dec); 1H-NMR (CDCl3) ∂7.35 (d, J=8.1 Hz, 1H), 7.31 (d, J=1.8 Hz, 1H), 7.05 (dd, J=1.8, 8.1 Hz, 1H), 3.14 (m, 1H), 2.80-2.91 (m, 2H), 2.67-2.80 (complex m, 4H), 2.58 (m, 1H), 2.48 (m, 1H), 2.24 (m, 1H), 2.15 (q, J=8.6 Hz, 1H), 1.89 (m, 1H), 1.73 (m, 2H), 1.60 (m, 2H° ), 1.07 (t, J=8.6 Hz, 3H); CIMS (MH+ calcd for C15H22Cl2N2): 301. Found (MH+): 301; Anal. (calcd for C17H24Cl2N2O·0.5H2O): C,H,N.
Sources & evidence
- ORD record
- ord-64583f82c37f46bda89bac94a03a6775
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05571832
Reaction notes
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