tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → Boc-L-leucinol

HRID 434482Notes

Reaction equation

HRID 434482 reaction equation
[C:1]([NH:8][C@H:9]([CH:14]=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[BH4-].[Na+]>CO>[C:1]([NH:8][C@H:9]([CH2:14][OH:15])[CH2:10][CH:11]([CH3:12])[CH3:13])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

4

Reactant 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 4311764Sodium borohydride

Product 1

HCID 7018766Boc-L-leucinolYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of BOC-leucinal (168 mg, 0.780 mmol) in methanol (2 ml) cooled to 0° C., was added sodium borohydride (30 mg, 0.780 mmol). After stirring 15 min, the reaction was complete by TLC. The methanol was removed in vacuo and the resulting residue slurried with water and extracted with ether (3×). The combined ethereal extracts were washed with saturated NaCl (aq) (2×), dried over MgSO4, and filtered. The filtrate was stripped to dryness in vacuo to give 130 mg of BOC-leucinol as a colorless oil with properties identical to those described above in Example 1, Step A.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionextracted with ether (3×)
  3. washThe combined ethereal extracts were washed with saturated NaCl (aq) (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7abee15dbd47486ab30ddc7e6eec07af
Source dataset
uspto-grants-1983_08
Patent number
US04397786

Reaction notes

Loading…