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

Melting point:

81.0 to 85.0 °C

Boiling point:

294.5±9.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

12.24±0.20(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C9H17NO3/c1-8(2,3)13-7(12)10-9(6-11)4-5-9/h11H,4-6H2,1-3H3,(H,10,12)

InChIKey

HFMAZNJKNNRONT-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1(CO)CC1

Safety Information

HS Code 

2924297099

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate Usage And Synthesis

Uses

Tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate could be converted into spirocyclopropanated analogues 14-CP and 14-CT of the insecticide Thiacloprid [1]. It can also be transformed into spirocyclopropanated analogs of Imidacloprid. This compound could be used to synthesize spirocyclopropanated five-membered ring analog 4-(3,5-Dichlorophenyl)-N-isopropyl-5-oxo-4,6-diazaspiro- [2.4]heptane-6-carboxamide[2].

Preparation

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].

References

[1] Brackmann F, et al. Synthesis of Spirocyclopropanated Analogues of Imidacloprid and Thiacloprid. European Journal of Organic Chemistry, 2005; 2005: 600-609.
[2] Brackmann F, et al. Synthesis of Spirocyclopropanated Analogues of Iprodione. European Journal of Organic Chemistry, 2005; 2005: 2250-2258.

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate(107017-73-2)Related Product Information

• 1-N-Boc-Aminocyclopentanecarboxylic acid
• 1-(Boc-amino)cyclopropanecarboxylic acid
• Cyclopropyl carbinol
• 1-AMINO-CYCLOPROPANEMETHANOL
• (1R,2S)-1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER
• 1-BOC-3-AMINOPIPERIDINE
• (1R,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID
• Cyclopropanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-, (1R,2S)-rel-
• tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate
• 1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER
• (1R,2S)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID
• VINYL ACCA
• BOC-1-AMINO-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID
• (1S,2S)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID
• (1S,5R)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-1-CARBOXYLIC ACID
• 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-,(1S,2R)-
• (1S,2R)-N-BOC-1-AMINO-2-PHENYLCYCLOPROPANECARBOXYLIC ACID
• (R)-BOC-1-AMINO-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACID