Sodium borohydride → 1,1-Dimethylethyl (2S)-4-{[2-chloro-4-(methylamino)phenyl]methyl}-2-methyl-1-piperazinecarboxylate

HRID 534784Notes

Reaction equation

HRID 534784 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)=[C:4]([Cl:23])[CH:3]=1.[CH3:24][C@H]1CN(CC2C=CC(NC)=CC=2)CCN1C(OC(C)(C)C)=O.[BH4-].[Na+]>>[Cl:23][C:4]1[CH:3]=[C:2]([NH:1][CH3:24])[CH:7]=[CH:6][C:5]=1[CH2:8][N:9]1[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]1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylateHCID 592621321,1-Dimethylethyl (2S)-4-[(4-amino-2-chlorophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Product 1

HCID 592621201,1-Dimethylethyl (2S)-4-{[2-chloro-4-(methylamino)phenyl]methyl}-2-methyl-1-piperazinecarboxylate

Conditions

Temperature
50 °C

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-4-[(4-amino-2-chlorophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D104) using a method similar to that described for D3 in Description 3A although the reaction was heated at 50° C. overnight prior to, and for 24 h after addition of sodium borohydride. (3 eq.). MS (ES): MH+ 354/356.

Sources & evidence

ORD record
ord-8857693096e543e4a804a3d454a87f03
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

Loading…