Hydrochloric Acid → HCID 67266052, compound

HRID 1685321Notes

Reaction equation

HRID 1685321 reaction equation
O=[CH:2][C:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH2:25]([NH2:30])[C:26]([CH3:29])([CH3:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-].[Na+].Cl>CN(C=O)C.COC(OC)OC.C(O)(=O)C.CO>[CH2:25]([NH:30][CH2:2][C:3]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 79882NeopentylamineHCID 4311764Sodium borohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 59200439HCID 59200439, compound

Product 1

HCID 67266052HCID 67266052, compoundYield 45.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of tert-butyl 3-oxo-2,2-diphenylpropylcarbamate (0.10 g, 0.307 mmol) in DMF (4 mL) and trimethylorthoformate (4 mL) was treated with neopentylamine (0.054 g, 0.615 mmol), sodium triacetoxyborohydride (0.098 g, 0.461 mmol) and acetic acid (2 drops) and the reaction was stirred at 23° C. overnight. LC/MS shows only formation of the imine. The reaction was then treated with sodium borohydride (0.050 g, 1.32 mmol) and methanol (˜2 mL) and stirred at 23° C. for 30 minutes. The reaction was acidified with 1N HCl and washed with diethyl ether. The aqueous phase was basified with sat. aq. sodium bicarbonate, extracted with diethyl ether (3×) and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude tert-butyl 3-(neopentylamino)-2,2-diphenylpropylcarbamate (0.055 g, 45%) as an oil. 1H NMR (400 MHz, CDCl3) δ: 0.82 (9H, s), 0.92-0.96 (2H, m), 1.42 (9H, s), 2.35 (2H, s), 3.47 (2H, s), 3.86 (2H, d, J=4.80 Hz), 7.15 (1H, br s), 7.17-7.26 (6H, m), 7.28-7.34 (4H, m). HPLC ret. time (Condition A): 2.68 min. LC/MS (M+H)+: 397.

Workup

  1. stirringstirred at 23° C. for 30 minutes
  2. washwashed with diethyl ether
  3. extractionextracted with diethyl ether (3×)
  4. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-583ebe3db2b04c9982f38fc60f24fc97
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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