ChemicalBook CAS DataBase List N-BOC-L-Prolinal

N-BOC-L-Prolinal synthesis

11synthesis methods

Product Name:N-BOC-L-Prolinal
CAS Number:69610-41-9
Molecular formula:C10H17NO3
Molecular Weight:199.25

69610-40-8 Synthesis

69610-40-8
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$6.00/5g

69610-41-9
256 suppliers
$9.00/1g

Yield:69610-41-9 99%

Reaction Conditions:

with oxalyl dichloride;dimethyl sulfoxide;triethylamine in dichloromethane

Steps:

64.a 64a
64a (S)-(+)-N-Boc-2-Prolinal To a solution of DMSO (5.86 mL, 75.8 mmol) in 120 mL of CH₂Cl₂ at -78° C. was added oxalyl chloride (4.40 mL, 50.4 mmol) dropwise. The solution was stirred 10 min and then a solution of (S)-(+)-N-Boc-2-Prolinol (5.08 g, 25.2 mmol) in 50 mL of CH₂Cl₂ was added dropwise. The solution was stirred 20 min and triethylamine (14.1 mL, 100 mmol) was added dropwise. The solution was warmed to room temperature and then stirred for 30 min. The solution was treated with 50 mL of water and extracted twice with 100 mL CH₂Cl₂. The organic layer was then dried over Na₂SO₄, filtered and concentrated under reduced pressure to give an oil. The oil was purified by silica gel chromatography with 25% EtOAc/Hexanes to give the title compound as a light yellow oil (5.0 g, 99%) ES (+) MS m/e=200 (M+H).

References:

SmithKline Beecham Corporation US6403792, 2002, B1

FullText

59936-29-7 Synthesis