Sodium borohydride → 1,1-Dimethylethyl (2R)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate
Reaction equation
NC1C=CC(CN2CCN(C(OC(C)(C)C)=O)[C@H](C)C2)=CC=1.[CH3:23][C@H:24]1[CH2:29][N:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][CH3:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26][N:25]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].[BH4-].[Na+]>>[CH3:23][C@@H:24]1[CH2:29][N:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][CH3:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26][N:25]1[C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40]Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 50 °C
Procedure
The title compound was prepared from 1,1-dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D5) using a method similar to that described for D3 in Description 3A although the reaction was heated at 50° C. for 48 h prior to addition of sodium borohydride. δH (CDCl3, 400 MHz) 7.13 (2H, d), 6.57 (2H, d), 4.16 (1H, m), 3.78 (1H, d), 3.42 (1H, d), 3.29 (1H, d), 3.08 (1H, td), 2.83 (3H, s), 2.75 (1H, m), 2.59 (1H, m), 2.07 (1H, dd), 1.94 (1H, m), 1.45 (9H, s), 1.21 (3H, d). MS (ES+): 342.3 (MNa+), 220.2, no molecular ion (MH+) observed.
Sources & evidence
- ORD record
- ord-795347ebbaf644488f4324a270994c43
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853218B2
Reaction notes
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