| Identification | More | [Name]
1-Boc-Pyrrolidine | [CAS]
86953-79-9 | [Synonyms]
1-BOC-PYRROLIDINE
N-T-BOC-PYRROLIDINE
PYRROLIDINE-N-BOC PROTECTED
TERT-BUTYL 1-PYRROLIDINECARBOXYLATE
1-(tert-Butoxycarbonyl)pyrrolidine
Pyrrolidine-1-carboxylicacidtert-butylester
N-T-Boc-Pyrrolidone
1-Boc-pyrrolidine,96%
N-Boc
n-boc-pyrrolidine
Pyrrolidine, N-BOC protected 97% | [EINECS(EC#)]
617-940-8 | [Molecular Formula]
C9H17NO2 | [MDL Number]
MFCD00216581 | [Molecular Weight]
171.24 | [MOL File]
86953-79-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
80 °C/0.2 mmHg (lit.) | [density ]
0.977 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.449(lit.)
| [Fp ]
187 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform, Methanol | [form ]
Oil | [pka]
-1.28±0.20(Predicted) | [color ]
Clear Colorless | [BRN ]
4664750 | [InChI]
InChI=1S/C9H17NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H2,1-3H3 | [InChIKey]
LPQZERIRKRYGGM-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCCC1 | [CAS DataBase Reference]
86953-79-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
NA 1993 / PGIII | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
liquid | [Uses]
N-Boc-pyrrolidine may be used in the synthesis of the following:
- 2-aryl-N-boc-pyrrolidines
- scalemic 2-pyrrolidinylcuprates
- 2-alkenyl-N-Boc-pyrrolidines
- 1-deoxycastanospermine
- methylphenidate analogues
- (+)-elaeokanine A
| [Uses]
1-Boc-pyrrolidine is a boc-protected cyclic amine used as a building block in the preparation of diastereomers by usually undergoing α'-lithiations and electrophilic substitution reactions.
| [General Description]
N-Boc-pyrrolidine is an N-substituted pyrrolidine. It is reported that the reactivity of N-Boc-pyrrolidine towards C-H insertion reaction is 2000 times more than cyclohexane. It undergoes α-arylation in the presence of a palladium catalyst with high enantioselectivity. | [Synthesis]
The general procedure for the synthesis of 1-Boc-tetrandrine from tetrandrine and di-tert-butyl dicarbonate is as follows: the synthesis was carried out by a modified literature method (omitting the Sparteine chiral ligand), as specified in J. Am. Chem. Soc. 1994, 116, 3231.The steps are as follows:
A) Preparation of Boc-protected pyrrolidines
Triethylamine (TEA, 15.6 g, 0.15 mol) was slowly added to a dichloromethane (DCM, 150 mL) solution of pyrrolidine (10.0 g, 0.14 mol) in stirring at 0 °C. Subsequently, di-tert-butyl dicarbonate ((Boc)2O, 30.6 g, 0.14 mol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete pyrrolidine consumption. Upon completion of the reaction, the reaction mixture was washed sequentially with 1 M aqueous hydrochloric acid (100 mL) and brine, and the organic phase was dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to afford the colorless, oily product 1-Boc-tetrandrine (24.0 g, 100%), which could be used in the subsequent steps without further purification. | [References]
[1] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2527 - 2532
[2] Patent: WO2013/102242, 2013, A1. Location in patent: Page/Page column 94; 95
[3] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8318 - 8322
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[5] Synthesis, 2001, # 4, p. 550 - 552 |
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