(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Chemical Properties

Boiling point:

308.8±42.0 °C(Predicted)

Density 

1.179

storage temp. 

2-8°C(protect from light)

pka

14.36±0.40(Predicted)

Appearance

White to off-white Solid

optical activity

2.4° (C=0.01 g/ml, ETOH)

InChI

InChI=1S/C9H18N2O3/c1-9(2,3)14-8(13)11-4-6(10)7(12)5-11/h6-7,12H,4-5,10H2,1-3H3/t6-,7-/m0/s1

InChIKey

MOZOQDNRVPHFOO-BQBZGAKWSA-N

SMILES

N1(C(OC(C)(C)C)=O)C[C@H](O)[C@@H](N)C1

(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Usage And Synthesis

Uses

(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine is used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine from the compound (CAS:1202067-33-1): trifluoroacetic acid (TFA, 3 drops) was added to a methanol (50 mL) solution of Intermediate 11 (5.1 g, 17.1 mmol) and the mixture was stirred for 2 hours. Subsequently, platinum oxide (100 mg, 0.44 mmol) was added to the mixture and stirred under hydrogen atmosphere for 18 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the solvent was removed by vacuum evaporation. The crude product was recrystallized by dichloromethane (DCM) to afford 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine as a white solid (2.42 g, 71% yield). NMR hydrogen spectral (CDCl3) data: δ 3.99 (1H, m), 3.70 (2H, m), 3.34 (2H, m), 3.12 (1H, m), 1.48 (9H, s).

References

[1] Patent: WO2009/153554, 2009, A1. Location in patent: Page/Page column 40

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