Carbamate → tert-butyl N-[(2S)-1-amino-4-methylpentan-2-yl]carbamate

HRID 1030632Notes

Reaction equation

HRID 1030632 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])N.CC([N:15]([C@H:19]([CH2:24][N:25]=[N+]=[N-])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:16](=[O:18])[O-:17])(C)C.OS([O-])(=O)=O.[Na+]>C1COCC1.O.CCOC(C)=O>[NH2:25][CH2:24][C@@H:19]([NH:15][C:16](=[O:18])[O:17][C:21]([CH3:23])([CH3:22])[CH3:20])[CH2:20][CH:21]([CH3:22])[CH3:23]

Participants

8

Reactant 4

HCID 276CarbamateHCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 86745708(S)-(-)-1,1-Dimethylethyl(1-azidomethyl-3-methylbutyl)carbamate

Product 1

HCID 10262776tert-butyl N-[(2S)-1-amino-4-methylpentan-2-yl]carbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (0.24 g; 6.4 mmole) was slurried in THF (20 mL) and cooled to 0° C. The suspension was treated with a solution of the carbamate from (c) above (1.1 g; 4.6 mmole) in THF (10 mL) and stirred for 2 hours at 0° C. The mixture was further cooled to -30° C. and a solution of NaHSO4 (0.6 g; 4.3 mmole) in H2O (5 mL) was cautiously added and then diluted with EtOAc (50 mL), and filtered through celite. The filtrate was dried over MgSo4, filtered, and concentrated in vacuo leaving a colorless liquid. Yield: 1.0 g (100%)

Workup

  1. temperatureThe mixture was further cooled to -30° C.
  2. filtrationfiltered through celite
  3. customThe filtrate was dried over MgSo4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customleaving a colorless liquid

Sources & evidence

ORD record
ord-e33e0b6498d845fc95486df0fc0f7f3f
Source dataset
uspto-grants-1992_04
Patent number
US05106873

Reaction notes

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