Tert-Butylamine → HCID 58124808, compound

HRID 1971712Notes

Reaction equation

HRID 1971712 reaction equation
[CH:1]([C:3]1[C:4]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:15][CH:16]([CH3:18])[CH3:17])[CH:13]=3)[CH2:8][CH2:7][N:6]2[C:21]=1[C:22]([OH:24])=[O:23])=O.[C:30]([NH2:34])([CH3:33])([CH3:32])[CH3:31].C([BH3-])#N.[Na+].[Na]>CO.C1COCC1.C(O)(=O)C>[C:30]([NH:34][CH2:1][C:3]1[C:4]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[C:5]2[C:14]3[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:15][CH:16]([CH3:18])[CH3:17])[CH:13]=3)[CH2:8][CH2:7][N:6]2[C:21]=1[C:22]([OH:24])=[O:23])([CH3:33])([CH3:32])[CH3:31]

Participants

8

Reactant 4

HCID 6385Tert-ButylamineHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 581249292-Formyl-5,6-dihydro-8-methoxy-9-(1-methylethoxy)-1-(2-thienyl)pyrrolo[2,1-a]isoquinoline-3-carboxylic acid

Product 1

HCID 58124808HCID 58124808, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg of 15d and 110 mg of tert-butyl amine in 20 ml of methanol and 5 ml of THF was added 140 mg of sodium cyanoborohydride and 90 mg of acetic acid. The mixture was stirred for 3 hr at RT, then 140 mg of sodium cycanoborohydride was added additionally and stirring was prolonged for 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by chromatography over silica gel, using a gradient of dichloromethane and methanol, to provide 520 mg of 15e; MS-ESI: [M+1] 469.23.

Workup

  1. stirringstirring
  2. waitwas prolonged for 16 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-1b70ab62271543dfa083d884b986e523
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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