Sodium borohydride → 1,1-Dimethylethyl (2S)-4-{[3-fluoro-4-(methylamino)phenyl]methyl}-2-methyl-1-piperazinecarboxylate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:11]([CH3:22])[CH2:10]2)=[CH:4][C:3]=1[F:23].[CH3:24][C@H]1CN(CC2C=CC(NC)=CC=2)CCN1C(OC(C)(C)C)=O.[BH4-].[Na+]>>[F:23][C:3]1[CH:4]=[C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C@@H:11]([CH3:22])[CH2:10]2)[CH:6]=[CH:7][C:2]=1[NH:1][CH3:24]Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 50 °C
Procedure
The title compound was prepared from 1,1-dimethylethyl (2S)-4-[(4-amino-3-fluorophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D63) using a method similar to that described for D3 in Description 3A although the reaction was heated at 50° C. overnight prior to and after addition of sodium borohydride. δH (CDCl3, 400 MHz) 6.96 (2H, m), 6.61 (1H, m), 4.17 (1H, br.s), 3.89 (1H, br.s), 3.79 (1H, d), 3.41 (1H, d), 3.28 (1H, d), 3.08 (1H, td), 2.87 (3H, s), 2.74 (1H, m), 2.57 (1H, m), 2.08 (1H, dd), 1.95 (1H, m), 1.45 (9H, s), 1.22 (3H, d).
Sources & evidence
- ORD record
- ord-3f16c7c3e1ac46eab58242206f94ce5e
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853218B2
Reaction notes
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