ChemicalBook CAS DataBase List tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate synthesis

9synthesis methods

Product Name:tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate
CAS Number:107017-73-2
Molecular formula:C9H17NO3
Molecular Weight:187.24

Tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate can be synthesized in three steps (40 % overall yield) from N, Ndibenzyl-2-benzyloxyacetamide starting with its reductive cyclopropanation (the de Meijere variant of the so-called Kulinkovich reaction). It can also be prepared in 56 % overall yield by monohydrolysis of commercially available diethyl cyclopropane-1,1-dicarboxylate followed by Curtius degradation of the carboxylic acid residue and subsequent reduction of the ester moiety[1].

24424-99-5 Synthesis

24424-99-5
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$13.50/25G

115652-52-3 Synthesis

1-Amino-1-(hydroxymethyl)cyclopropane hydrochloride

115652-52-3
138 suppliers
$8.00/100mg

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

107017-73-2
188 suppliers
$8.00/100mg

Yield:107017-73-2 100%

Reaction Conditions:

Stage #1: 1-amino-1-(hydroxymethyl)cyclopropane hydrochloridewith triethylamine in tetrahydrofuran at 0; for 0.166667 h;
Stage #2: di-tert-butyl dicarbonate in tetrahydrofuran at 0 - 20;

Steps:

20.1 Step 1tert-butyl N-[1-(hydroxymethyl)cyclopropyl]carbamate (20B)

Triethylamine (4.93 g,48.76 mmol) was added dropwise to a stirred solution of (1- aminocyclopropyl)methanol hydrochloride(20A) (2 g,16.25 mmol) in THF (50 mL) at 0°C. After 10 min of stirring, di-tert-butyl dicarbonate (7.09 g,32.50mmol) in THF (5 mL) was added dropwise to the mixture at 0°C. The mixture was stirred overnight in room temperature, the solvent was removed in vacuo. The residue was diluted with ethyl acetate (60 mL), washed with water (2×60 mL) and brine (50 mL), dried with Na₂SO₄ and concentrated. then the title compound (20B) (3g.100%) was obtained as white solid, which was used in the next step without further purification.¹H NMR (400 MHz, CDCl₃) d 5.05 (s, 1H), 3.59 (s, 2H), 2.40 (s, 1H), 1.44 (s, 9H), 0.83 (m, 4H).

References:

WO2020/185755,2020,A1 Location in patent:Paragraph 00392

88950-64-5 Synthesis