Dimethyl Sulfoxide → (S)-2-Boc-aminobutyraldehyde

HRID 1444577Notes

Reaction equation

HRID 1444577 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C@@H:18]([CH2:22][CH3:23])[CH:19](N)[OH:20])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([N:26](CC)CC)C.P([O-])(O)(O)=O.[Na+]>C(Cl)Cl>[C:11]([C@:18]([NH2:26])([CH2:22][CH3:23])[CH:19]=[O:20])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23672064Monosodium phosphateHCID 866023542(S)-Boc-aminobutanol

Product 1

HCID 86590935(S)-2-Boc-aminobutyraldehydeYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-60 °C

Procedure

A solution of oxalyl chloride (40.39 g, 265 mmol) in MeCl2 (700 mL) was stirred and cooled to −60° C. Dimethylsulfoxide (51.7 g, 663 mmol) in MeCl2 (100 mL) was added dropwise. After 10 min., a solution of 2(S)-Boc-amino-1-butanol (50 g, 265 mmol) in MeCl2 (100 mL) was added dropwise at −70° C. The reaction mixture was allowed to warm to −40° C. for 10 min. and then cooled to −70° C. again. A solution of triethylamine (74.9 g, 742 mmol) in MeCl2 (100 mL) was added. The reaction mixture was allowed to warm to room temperature over 2 h. Saturated sodium dihydrogen phosphate (100 mL) was added, and then the organic layer was washed with brine and dried over MgSO4. The solvent was removed to yield 45 g of 2(S)-Boc-aminobutyraldehyde.

Workup

  1. temperatureto warm to −40° C. for 10 min.
  2. temperaturecooled to −70° C. again
  3. temperatureto warm to room temperature over 2 h
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-22262693cce1482a882c65b1e77b50b8
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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