Sodium borohydride → tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylate

HRID 534763Notes

Reaction equation

HRID 534763 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]([CH3:23])[CH:3]=1.[CH3:24][C@H]1CN(CC2C=CC(NC)=CC=2)CCN1C(OC(C)(C)C)=O.[BH4-].[Na+]>>[CH3:22][C@H:11]1[CH2:10][N:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][CH3:24])=[CH:3][C:4]=2[CH3:23])[CH2:14][CH2:13][N:12]1[C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16]

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 59262126tert-butyl (2S)-4-[(4-amino-2-methylphenyl)methyl]-2-methylpiperazine-1-carboxylateHCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

Product 1

HCID 59262129tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylate

Conditions

Temperature
50 °C

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-4-[(4-amino-2-methylphenyl)methyl]-2-methyl-1-piperazinecarboxylate (D80) using a method similar to that described for D3 in Description 3A although the reaction was heated at 50° C. for 16 h prior to addition of sodium borohydride and 5.5 h after addition. δH (CDCl3, 400 MHz) 7.00 (1H, d), 6.45 (1H, d), 6.39 (1H, dd), 4.17 (1H, br.s), 3.76 (1H, d), 3.57 (1H, br.s), 3.33 (1H, d), 3.27 (1H, d), 3.01 (1H, td), 2.82 (3H, s), 2.71 (1H, d), 2.58 (1H, d), 2.32 (3H, s), 2.11 (1H, dd), 1.90 (1H, m), 1.45 (9H, s), 1.17 (3H, d). MS (AP+): 356.2 (MNa+), 234.2, no molecular ion (MH+) observed.

Workup

  1. additionafter addition

Sources & evidence

ORD record
ord-a5dc10705ce24e0495243b93c7976ab8
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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