1-Acetylpiperazine → HCID 69067028, compound

HRID 1726383Notes

Reaction equation

HRID 1726383 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[C:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])[CH3:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH2:9][N:19]1[CH2:20][CH2:21][N:16]([C:13](=[O:15])[CH3:14])[CH2:17][CH2:18]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 837951-AcetylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Product 1

HCID 69067028HCID 69067028, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(R)-(1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (1.85 g, 10.7 mmole) and acetyl piperazine (1.53 g, 12 mmole) were combined in dichloroethane (125 mL). NaBH(OAc)3 (4.53 g. 21 mmole) was added. The resultant reaction solution was stirred at room temperature for 20 h. An equal volume of saturated NaHCO3 was added. The aqueous phase was extracted 3 times with CH2Cl2. The combined organic extracts were washed with saturated NaCl, dried over Na2SO4 and concentrated under vacuum. Purification by silica chromatography (5% methanol in CH2Cl2 provided (R)-[2-(4-acetylpiperazin-1-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (Intermediate XXIXa, 2.6 g)

Workup

  1. customThe resultant reaction solution
  2. extractionThe aqueous phase was extracted 3 times with CH2Cl2
  3. washThe combined organic extracts were washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customPurification by silica chromatography (5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-0e57db2e25ab4001b3874c975e3d9e36
Source dataset
uspto-grants-2009_02
Patent number
US07491821B2

Reaction notes

Loading…