Sodium triacetoxyborohydride → [2-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-carbamic acid t-butyl ester

HRID 553486Notes

Reaction equation

HRID 553486 reaction equation
[C:1]([O:5][C:6](=[O:12])[N:7]([CH3:11])[CH2:8][CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[C:15]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[N:16][CH:17]=[CH:18][N:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:8][CH2:9][N:23]1[CH2:24][CH2:25][N:20]([C:15]2[C:14]([Cl:13])=[N:19][CH:18]=[CH:17][N:16]=2)[CH2:21][CH2:22]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 140864382-Chloro-3-(piperazin-1-yl)pyrazine

Product 1

HCID 59252215[2-(3'-Chloro-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl)-ethyl]-methyl-carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Add methyl-(2-oxo-ethyl)-carbamic acid t-butyl ester (27.69 mmoles; 4.80 g) and 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazine (25.17 mmoles; 5.00 g) to 1,2 dichloroethane (50.0 mL) on ice. Add sodium triacetoxyborohydride (32.7 mmoles; 6.93 g) in 3 portions. Stir the reaction mixture at room temperature overnight. Quench the reaction with water, separate the organic layer and concentrate. Wash in hexanes and filter to provide [2-(3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl)-ethyl]-methyl-carbamic acid t-butyl ester as a clear oil.

Workup

  1. customQuench
  2. customthe reaction with water
  3. customseparate the organic layer
  4. concentrationconcentrate
  5. washWash in hexanes
  6. filtrationfilter

Sources & evidence

ORD record
ord-ece5dbd1a3d24e7a9a6c924d6fc0c337
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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