Diisopropylamine → HCID 69198941, compound

HRID 1394208Notes

Reaction equation

HRID 1394208 reaction equation
Cl.[CH:2]1[C:14]2[CH:13]([CH2:15][O:16][C:17]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[C:32]([O:36][C:37](=[O:43])[NH:38][CH2:39][CH2:40][CH:41]=O)([CH3:35])([CH3:34])[CH3:33].C([BH3-])#N.[Na+]>CO>[CH:2]1[C:14]2[CH:13]([CH2:15][O:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:41][CH2:40][CH2:39][NH:38][C:37]([O:36][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:43])[CH2:21][CH2:20]3)=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 2756142Fmoc-piperazine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 10910051tert-Butyl N-(3-oxopropyl)carbamate

Product 1

HCID 69198941HCID 69198941, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Piperazine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester hydrochloride (0.67 g, 1.93 mmole) was dissolved in methanol (5 ml), treated with diisopropylamine (0.34 m], 1.93 mmole) and allowed to stir at room temperature for 5 minutes. The product from Step 1 (0.50 g, 2.89 mmole) and sodium cyanoborohydride (133 mg, 2.12 mmole) were added and the mixture stirred under argon for 18 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography eluting with ethyl acetate/hexane (1:1) to afford the title compound (0.71 g). 1H NMR (CDCl3) δ 7.78-7.75 (2H, d), 7.59-7.56 (2H, d), 7.41-7.31 (4H, m), 4.52-4.43 (2H, d), 4.27-4.20 (1H, t), 3.51-3.42 (4H, br m), 3.25-3.15 (2H, m), 2.45-2.35 (6H, m), 1.72-1.60 (2H, m), 1.45 (9H, s).

Workup

  1. stirringthe mixture stirred under argon for 18 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-e059a8f23e6e4c36a0f6d9bbaa77f4d8
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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