Ethyl Acetate → HCID 68162283, compound

HRID 2366829Notes

Reaction equation

HRID 2366829 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:29])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=3)[CH:15]=2)[N:10]([C:25](=[O:27])[CH3:26])[C@@H:9]([CH3:28])[CH2:8]1)[CH3:3].[N:30]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClCCl.CCCC(C)C>[C:25]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:33]4[CH2:34][CH2:35][N:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31][CH2:32]4)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5]([O:4][CH:2]([CH3:3])[CH3:1])=[O:29])[CH2:8][C@@H:9]1[CH3:28])(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86669228HCID 86669228, compound

Product 1

HCID 68162283HCID 68162283, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 78922-MethylpentaneSolvent

Procedure

1-methylethyl[(cis)-1-acetyl-6-(4-formylphenyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 7) (95 mg, 0.241 mmol) was dissolved in Dichloromethane (DCM) (2 mL) and to this was added tert-butyl 1 piperazinecarboxylate (67.3 mg, 0.361 mmol) as a solid and the resulting solution stirred under nitrogen for 40 min. sodium triacetoxyborohydride (66.4 mg, 0.313 mmol) was added and stirred as a suspension over the weekend. The reaction was quenched with ammonium chloride (2 ml). The organics were separated and the aqueous reextracted with DCM (5 ml). The combined organics were washed with water (5 ml) and reduced in vacuo to give a colourless solid. (135 mg). The solid was dissolved in DCM and loaded onto a 12+M silica cartridge for automated flash chromatography. A gradient of 20 to 100% ethyl acetate in iso-hexane over 10 CV was used and the appropriate fractions reduced in vacuo to give a colourless oil which was dried on high vac overnight (98 mg).

Workup

  1. additionwas added
  2. customThe reaction was quenched with ammonium chloride (2 ml)
  3. customThe organics were separated
  4. washThe combined organics were washed with water (5 ml)
  5. customto give a colourless solid
  6. customto give a colourless oil which
  7. customwas dried on high vac overnight (98 mg)

Sources & evidence

ORD record
ord-ea93f329a8a5412c956f9bab6454560a
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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