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427055

Sigma-Aldrich

N-Boc-pyrrolidine

97%

동의어(들):

tert-Butyl 1-pyrrolidinecarboxylate

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About This Item

실험식(Hill 표기법):
C9H17NO2
CAS Number:
86953-79-9
Molecular Weight:
171.24
MDL number:
MFCD00216581
UNSPSC 코드:
12352100
PubChem Substance ID:
24866734
NACRES:
NA.22

분석

97%

형태

liquid

refractive index

n20/D 1.449 (lit.)

bp

80 °C/0.2 mmHg (lit.)

density

0.977 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)N1CCCC1

InChI

1S/C9H17NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H2,1-3H3

InChI key

LPQZERIRKRYGGM-UHFFFAOYSA-N

일반 설명

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.

애플리케이션

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

픽토그램

Exclamation mark
GHS07

신호어

Warning

유해 및 위험 성명서

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

표적 기관

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

186.8 °F - closed cup

Flash Point (°C)

86 °C - closed cup

개인 보호 장비

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

시험 성적서(COA)

제품의 로트/배치 번호를 입력하여 시험 성적서(COA)을 검색하십시오. 로트 및 배치 번호는 제품 라벨에 있는 ‘로트’ 또는 ‘배치’라는 용어 뒤에서 찾을 수 있습니다.

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Sigma-Aldrich

461350

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Sigma-Aldrich

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Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites.
Davies HML, et al.
Bioorganic & Medicinal Chemistry Letters, 14(7), 1799-1802 (2004)
Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine.
Majewski M, et al.
Tetrahedron Letters, 39(38), 6787-6790 (1998)
Copper mediated scalemic organolithium reagents in alkaloid syntheses.
3Dieter RK, et al.
Tetrahedron, 61(13), 3221-3230 (2005)
Graeme Barker et al.
The Journal of organic chemistry, 76(15), 5936-5953 (2011-07-01)
A comprehensive study of the enantioselective Pd-catalyzed α-arylation of N-Boc pyrrolidine has been carried out. The protocol involves deprotonation of N-Boc pyrrolidine using s-BuLi/(-)-sparteine in TBME or Et(2)O at -78 °C, transmetalation with ZnCl(2) and Negishi coupling using Pd(OAc)(2), t-Bu(3)P-HBF(4)
Catalytic asymmetric C-H activation by methyl thiophen-3-yldiazoacetate applied to the synthesis of (+)-cetiedil.
Davies HML, et al.
Tetrahedron Letters, 43(28), 4981-4983 (2002)
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