Benzyl 1,3-dihydro-5-(hydroxymethyl)-2H-isoindole-2-carboxylate, 2-[(Benzyloxy)carbonyl]-5-(hydroxymethyl)isoindoline synthesis
- Product Name:Benzyl 1,3-dihydro-5-(hydroxymethyl)-2H-isoindole-2-carboxylate, 2-[(Benzyloxy)carbonyl]-5-(hydroxymethyl)isoindoline
- CAS Number:1019889-84-9
- Molecular formula:C17H17NO3
- Molecular Weight:283.32
Yield:1019889-84-9 100%
Reaction Conditions:
Wilkinson's catalyst in toluene at 55 - 65; for 1 h;Product distribution / selectivity;
Steps:
81.7
A solution of propargyl alcohol (2.11 Kg, 37.7 mol) in toluene (32.48L) was degassed and heated to 55 0C. The solution of di-prop-2-ynyl-carbamic acid benzyl ester (4.06 Kg, 17.86 mol, step 6) in toluene and Wilkinsons catalyst (0.162 Kg) were added in 10 equal portions such that temperature <65 0C (the exotherm was allowed to subside before the next addition was made). The solution was then stirred at 55 0C for 1 h and then cooled to 20 0C. DCM (8.12 L) was added and the mixture was concentrated to a small volume. Toluene (8L) was added and the solution evaporated to constant weight giving the title compound 5.72 Kg (113%).
References:
WO2008/44041,2008,A1 Location in patent:Page/Page column 293-294
13139-17-8
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