Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Boiling point:

321℃

Density 

1.08

Flash point:

148℃

storage temp. 

2-8°C

pka

12.27±0.40(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-7-4-5-8(12)6-7/h7-8,12H,4-6H2,1-3H3,(H,11,13)/t7-,8+/m0/s1

InChIKey

SBUKINULYZANSP-JGVFFNPUSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@H]1CC[C@@H](O)C1

Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Uses

In asymmetric synthesis, the synthesis of chiral catalysts or chiral auxiliaries is crucial. Chiral amino alcohols are widely used as ligands or catalysts for catalyzing asymmetric synthetic reactions and are also important precursors for the synthesis of many chiral drugs, natural products, and chemical and biological functional materials.

Synthesis

Tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (8.0 g, 40.56 mmol, 1.00 eq.) was mixed with palladium/carbon catalyst (0.5 g) in methanol (100 mL). The reaction was stirred at 60 °C for 48 hours under hydrogen atmosphere. Upon completion of the reaction, the mixture was cooled to room temperature and the catalyst was removed by filtration. The catalyst was washed with methanol (3 x 10 mL). The filtrate and washings were combined and concentrated in vacuum to give tert-butyl N-[(1S,3R)-3-hydroxycyclopentyl]carbamate (6.5 g, 80% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, D2O, ppm): δ 4.72 (1H, s), 4.55 (1H, s), 1.92-1.87 (3H, m), 1.76-1.60 (3H, m), 1.50 (9H, s).

References

[1] Patent: WO2013/155338, 2013, A2. Location in patent: Page/Page column 144
[2] Patent: US2015/329503, 2015, A1. Location in patent: Paragraph 0646

Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI)(167465-99-8)Related Product Information

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